Derek Harold Richard Barton

Publié le lundi  31 août 2009
Mis à jour le mardi  1er juillet 2014 à 15h03min
par  Boivin Jean
popularité : 100%

Biographies

Sir Derek Harold Richard Barton FRS (8 September 1918 – 16 March 1998) was a British organic chemist and Nobel Prize laureate.

Barton was born to William Thomas and Maude Henrietta Barton. In 1938 he entered Imperial College London, where he graduated in 1940 and obtained his Ph.D. degree in Organic Chemistry in 1942. From then to 1944 he was a government research chemist, from 1944 to 1945 he was with Albright and Wilson in Birmingham. He then became assistant lecturer in the Department of Chemistry of Imperial College, and from 1946 to 1949 he was ICI Research Fellow. During 1949 and 1950 he was Visiting Lecturer in the Chemistry of Natural Products, at Harvard University, and was then appointed Reader in Organic Chemistry and, in 1953, Professor at Birkbeck College. In 1955 he became Regius Professor of Chemistry at the University of Glasgow, in 1957 he was appointed Professor of Organic Chemistry at Imperial College.

In 1950, Professor Barton showed that organic molecules could be assigned a preferred conformation based upon results accumulated by chemical physicists, in particular by Odd Hassel. Using this new technique of "conformational analysis", he later determined the geometry of many other natural product molecules. In 1969, Barton was awarded the Nobel Prize in Chemistry for "contributions to the development of the concept of conformation and its application in chemistry."

In 1958 Prof. Barton was Arthur D. Little Visiting Professor at Massachusetts Institute of Technology, and in 1959 Karl Folkers Visiting Professor at the Universities of Illinois and Wisconsin.

In 1954 he was elected to Fellowship of the Royal Society and the International Academy of Science, in 1956 he became Fellow of the Royal Society of Edinburgh ; in 1965 he was appointed member of the Council for Scientific Policy. He was knighted in 1972 but chose to be known as Sir Derek only in Britain. In 1978 he became Director of the Institut de Chimie des Substances Naturelles (ICSN - Gif Sur-Yvette) in France.

In 1986 he became Distinguished Professor at Texas A&M and held this position for 12 years until his death.

As well as for his work on conformation, his name is remembered in a number of reactions in organic chemistry such as the Barton-McCombie deoxygenation.

He married three times, and had a son by his first marriage. He died in College Station, Texas.

* F. Albert Cotton (2000). "Derek H. R. Barton, 8 September 1918 · 16 March 1998". Proceedings of the American Philosophical Society 144 (3) : 291–296. http://links.jstor.org/sici?sici=0003-049X%28200009%29144%3A3%3C291%3ADHRB8S%3E2.0.CO%3B2-Y.
* Steven V. Ley ; Rebecca M. Myers (2002). "Sir Derek Harold Richard Barton 8 September 1918—16 March 1998". Biographical Memoirs of Fellows of the Royal Society 48 : 1–23. doi:10.1098/rsbm.2002.0001. http://links.jstor.org/sici?sici=0080-4606%28200212%2948%3C1%3ASDHRB8%3E2.0.CO%3B2-

* Barton’s Nobel Foundation biography
* Barton’s Nobel Lecture The Principles of Conformational Analysis
* Video podcast of Barton talking about conformational analysis
* MDPI biography


Derek Harold Richard Barton was born on 8 September 1918, son of William Thomas and Maude Henrietta Barton. In 1938 he entered Imperial College, University of London, where he obtained his B.Sc.Hons. (1st Class) in 1940 and Ph.D. (Organic Chemistry) in 1942. From 1942 to 1944 he was a research chemist on a government project, from1944-1945 he was with Messrs. Albright and Wilson, Birmingham. In 1945 he became assistant lecturer in the Department of Chemistry of Imperial College, from 1946-1949 he was I.C.I. Research Fellow. In 1949 he obtained his D.Sc. from the same University. During 1949-1950 he was Visiting Lecturer in the Chemistry of Natural Products, at the Department of Chemistry, Harvard University (U.S.A.). In 1950 he was appointed Reader in Organic Chemistry and in 1953 Professor at Birkbeck College. In 1955 he became Regius Professor of Chemistry at the University of Glasgow, in 1957 he was appointed Professor of Organic Chemistry at Imperial College, which position he still holds.

In 1950, in a brief paper in Experientia entitled "The Conformation of the Steroid Nucleus", Professor Barton showed that organic molecules in general and steroid molecules in particular could be assigned a preferred conformation based upon results accumulated by chemical physicists, in particular by Odd Hassel. Having chosen a preferred conformation, it was demonstrated that the chemical and physical properties of a molecule could be interpreted in terms of that preferred conformation. In molecules containing fixed rings, such as the steroids, there resulted a simple relationship between configuration and conformation, such that configurations could be predicted once the possible conformations for the products of a reaction could be analysed. Thus the subject "conformational analysis" had begun. Barton later determined the geometry of many other natural product molecules using this method. Conformational analysis is useful in the elucidation of configuration, in the planning of organic synthesis, and in the analysis of reaction mechanisms. It will be fundamental to a complete understanding of enzymatic processes.

Prof. Barton was invited to deliver the following special lectures : 1956, Max Tischler Lecturer at Harvard University ; 1958, First Simonsen Memorial

Lecturer of the Chemical Society ; 1961, Falk-Plaut Lecturer, Columbia University ; 1962, Aub Lecturer at Harvard Medical School ; Renaud Lecturer at Michigan State University ; Inaugural 3 M’s Lecturer, University of Western Ontario ; 1963, Hugo Müller Lecturer of the Chemical Society ; 3 M’s Lecturer at the University of Minnesota ; 1967, Pedler Lecturer of the Chemical Society ; 1969, Sandin Lecturer at the University of Alberta ; 1970, Graham Young Lectureship, Glasgow.

In 1958 Prof. Barton was Arthur D. Little Visiting Professor at Massachusetts Institute of Technology, Cambridge, Mass. ; in 1959 Karl Folkers Visiting Professor at the Universities of Illinois and Wisconsin.

In 1954 Derek Barton was elected to Fellowship of the Royal Society, in 1956 he became Fellow of the Royal Society of Edinburgh ; in 1965 he was appointed member of the Council for Scientific Policy of the U. K. ; in 1969 he became President of Section B, British Association for the Advancement of Science, and President of the Organic Chemistry Division of the International Union of Pure and Applied Chemistry.

Professor Barton holds the following honours and awards : 1951, First Corday-Morgan Medal of the Chemical Society ; 1956, Fritzsche Medal of the American Chemical Society ; 1959, First Roger Adams Medal of the American Chemical Society ; 1960, Foreign Honorary Member of the American Academy of Arts and Sciences ; 1961, Davy Medal of the Royal Society ; 1962, D. Sc.h.c. Montpellier ; 1964, D. Sc.h.c. Dublin ; 1967, Honorary Fellow of the Deutsche Akademie der Naturforscher "Leopoldina" ; 1969, Honorary Member of Sociedad Quimica de Mexico ; 1970, D.Sc.h.c. St. Andrews : Fellow of Birkbeck College ; Honorary Member of the Belgian Chemical Society ; Foreign Associate of the National Academy of Sciences ; Honorary Member of the Chilean Chemical Society ; D.Sc.h.c., Columbia University, New York ; 1971, First award in Natural Product Chemistry, Chemical Society (London) ; D.Sc.h.c., Coimbra (Portugal) ; Elected Foreign Member of the Academia das Ciencias de Lisboa ; 1972, D. Sc.h.c. University of Oxford ; Longstaff Medal of the Chemical Society.

Derek Barton was first married to Jeanne Kate Wilkins but this marriage was later dissolved. He is now married to Christiane Cognet, a Professor of the Lycée français de Londres. He has one son, W.G.L. Barton, by his first marriage.

From Nobel Lectures, Chemistry 1963-1970, Elsevier Publishing Company, Amsterdam, 1972

This autobiography/biography was written at the time of the award and first published in the book series Les Prix Nobel. It was later edited and republished in Nobel Lectures. To cite this document, always state the source as shown above.

For more updated biographical information, see :
Barton, Derek H.R., Some Recollections of Gap Jumping. Oxford University Press, Oxford, 1998.

Sir Derek Barton died on March 16, 1998.


Barton, Derek (1918-1998), a British chemist, investigated natural organic compounds. He carried out research into conformational analysis, a method to study the three-dimensional shapes of molecules. Barton demonstrated how the shape of a molecule affects its physical and chemical properties. Conformational analysis gives scientists a tool to interpret chemical information and has proven useful in solving biochemical problems, especially in the area of pharmacology. For his groundbreaking findings, Barton shared the 1969 Nobel Prize in chemistry with Norwegian Odd Hassel .
Derek Harold Richard Barton was born to William Thomas Barton and Maude Barton. Barton’s father owned a successful lumberyard and was able to send his son to private school. Barton excelled in his classes at Tonbridge School, but his education ended abruptly when he was 17 and his father died. Barton dropped out of school without having received his diploma to assist his mother with the family business. But after two years, he became bored and returned to school. He enrolled at Gillingham Technical College, which he attended for a year before transferring to Imperial College of Science and Technology, University of London. To make financial ends meet, Barton commuted four hours a day to save money on living expenses. Barton received a B.S. degree from Imperial College of Science and Technology, London University in 1940.
Working under the supervision of prominent organic chemists, Ian Morris Heilborn and Ewart R. H. Jones, Barton earned his doctorate degree in organic chemistry in only two years. At the time, World War II (1939-1945) was being fought across Europe but Barton was unable to serve in active duty due to a minor heart defect. Instead, he was recruited to work in military intelligence. Staying on at Imperial College, Barton spent two years researching inks that could be used by the military for secret communication. In addition to his regular duties, Barton volunteered for an assignment to raise 10,000 beetles and study their chemical excretions.
In 1944, Barton accepted a position as a research chemist for an industrial firm in Birmingham, but he returned to Imperial College a year later as an assistant lecturer in chemistry. Initially, Barton taught inorganic and physical chemistry but switched to organic chemistry when a position opened. Between 1946 and 1949, he received a fellowship that allowed him to investigate the structures of organic molecules, including steroids. Steroids are a group of chemical compounds, including hormones, that play key roles in body processes. In the course of his studies, Barton designed models that accurately depicted the geometry of the steroid molecules. Barton used these models to explain the three-dimensional geometry of steroids. For this line of research, Barton earned a second doctorate in 1949.
In the late 1940’s, Louis Fieser, a professor of organic chemistry at Harvard University and a leading expert on steroids, became aware of Barton’s work and invited the English scientist to spend a year as a visiting lecturer. While at Harvard, Barton investigated the relationship between the reaction rates of steroids and the physical structure of their molecules. He wrote a four-page paper and submitted it to Experientia, a Swiss journal with a modest circulation. The paper, published in 1950, outlined Barton’s findings on conformational analysis, which served as the basis for his Nobel Prize.
For his study of steroids, Barton built on the work of Odd Hassel, a Norwegian chemist. Hassel had investigated the geometry of compounds with six carbon atoms, whose basic shape is a ring pattern. When a six-carbon ring is twisted, it can assume a shape that looks like a boat or a chair. Hassel demonstrated that when a six-carbon ring is at rest, it prefers the chair configuration because it is an energy-efficient configuration. Barton expanded Hassel’s findings to the study of more complex molecules and was able to describe why some molecular arrangements are more stable than others.
Before the publication of Barton’s paper, scientists had known about three-dimensional molecular structure but did not fully understand it. Consequently, they viewed molecules as two-dimensional. Adding a third dimension led to a greater understanding of molecular interactions. Barton’s paper gave scientists a powerful research aid. His principles soon became a standard part of the basic curriculum in undergraduate organic chemistry classes.
After a year at Harvard, Barton returned to England and became a reader and then a professor of organic chemistry at Birkbeck College, University of London. In 1955, he left London to accept a job as regius professor of Chemistry at the University of Glasgow. Two years later, he joined the faculty at the Imperial College of Science and Technology, University of London and served as a professor of organic chemistry until 1970 and then as Hoffmann professor of organic chemistry from 1970 until his retirement in 1978.
In 1977, Barton moved to Gif-sur-Yvette, France, to assume the duties as director of research at the Institute for the Chemistry of Natural Substances. In 1986, Barton left France to accept an appointment as distinguished professor at Texas A&M University in College Station, Texas, where he remained until his death in 1998.
Although Barton pioneered conformational analysis, he was active in a number of other areas. He investigated many natural chemicals, including morphine. He devised a method to successfully synthesize aldostrene, a hormone that helps to regulate kidney function. He also focused much of his research on inventing methods to produce new reactions. As a result, five chemical reactions are named in his honor. Although his research interests were varied, Barton stayed current with scientific developments by reading literature and staying in contact with other chemists. He also worked closely with his research assistants, checking their progress on a regular basis.
Barton had a long and distinguished career. In recognition of his achievements to the field of chemistry, he received many honors and awards, including the Corday-Morgan Medal of the Chemical Society of London (1951), the Fritzsche Award (1956), the Roger Adams Award of the American Chemical Society (1959), the Davy Medal of the Royal Society (1961), and the Royal Medal (1972). In 1995, he became the first faculty member from Texas A&M to win the Priestley Medal of the American Chemical Society. Barton was a fellow of the Royal Society and a foreign member of the American Academy of Arts and Sciences. He held honorary degrees from several universities, including Columbia and Oxford. In 1972, Barton was knighted.
Barton enjoyed speaking and traveled across the United States giving lectures and seminars. Barton was also a prolific author, writing over 1,000 scientific articles and books.
Barton married Jeanne Kate Wilkins in 1944 and the couple had a son. The marriage ended in divorce. Barton’s second wife was Christiane Cognet, a professor at the Lycée Français de Londres, who died in 1994. Barton was survived by his third wife, Judith Cobb Barton.

Source


Born : 8-Sep-1918
Birthplace : Gravesend, Kent, England
Died : 16-Mar-1998
Location of death : College Station, TX
Cause of death : unspecified
Gender : Male
Race or Ethnicity : White
Sexual orientation : Straight
Occupation : Chemist
Nationality : England
Executive summary : Conformational analysis
English chemist Derek Barton won the 1969 Nobel Prize for Chemistry, shared with Norwegian chemist Odd Hassel. Barton’s 1950 breakthrough in conformational analysis (study of the geometries and their associated energies for a given molecule) proposed that the rates of reaction in isomers are affected by the orientations in space of functional groups, and laid the groundwork for determining the three-dimensional shape of organic compounds. He also developed a new and simpler method of synthesizing the hormone aldosterone (vital for the treatment of Addison’s disease), and conducted research into the oxidation of saturated hydrocarbons and the behavior of oxyradicals.
Father : William Thomas Barton (carpenter)
Mother : Maude Henrietta Barton
Wife : Jeanne Kate Wilkins (m. 1944, div., one son)
Son : W. G. L. Barton
Wife : Christiane Cognet (university professor, m. 1969, d. 1992)
Wife : Judith Cobb (m. 1993)
High School : Tonbridge School, Kent, England (1936)
University : Gillingham Technical College, Gillingham, England (attended)
University : BS Chemistry, Imperial College London (1940)
University : PhD Chemistry, Imperial College London (1942)
University : DSc Chemistry, Imperial College London (1950)
Teacher : Chemistry, Imperial College London (1945-46)
Teacher : Organic Chemistry, Birkbeck College, University of London (1950-53)
Professor : Organic Chemistry, Birkbeck College, University of London (1953-55)
Professor : Regius Professor of Chemistry, University of Glasgow (1955-57)
Professor : Organic Chemistry, Imperial College London (1957-70)
Professor : Hofmann Professor of Organic Chemistry, Imperial College London (1970-78)
Administrator : Institute of Chemistry of Natural Substances, Gif-sur-Yvette, France (1978-86)
Professor : Distinguished Professor of Chemistry, Texas A&M University (1986-95)
Professor : Dow Distinguished Professor of Chemical Invention, Texas A&M University (1995-98)
Imperial Chemical Industries Research (1946-49)
Guinness Research, Distillers Co Ltd. (1940-42)
RSC Corday-Morgan Prize 1951
ACS Fritzsche Award 1956
ACS Roger Adams Medal 1960
Davy Medal 1961
Nobel Prize for Chemistry 1969 (with Odd Hassel)
RSC Longstaff Prize 1972
Royal Medal 1972
Knight of the British Empire 1972
Copley Medal 1980
Priestley Medal 1995
French Legion of Honor
American Academy of Arts and Sciences Foreign Member
American Chemical Society Foreign Member
British Association for the Advancement of Science
German Academy of Sciences Leopoldina Foreign Member, 1967
International Union of Pure and Applied Physics
National Academy of Sciences Foreign Associate
Royal Society 1954
Royal Society of Edinburgh 1956
English Ancestry
Author of books :
Comprehensive Organic Chemistry (1979, textbook ; with W. D. Ollis)
Some Recollections of Gap Jumping (1991, science)
Half a Century of Free Radical Chemistry (1993, science ; with Shyamal I. Parekh)
Reason and Imagination : Reflections on Research in Organic Chemistry (1996, science)

Source


JPEG - 12.7 ko

Article from the Encyclopædia Britannica

Sir Derek H.R. Barton, in full Sir Derek Harold Richard Barton (born September 8, 1918, Gravesend, Kent, England—died March 16, 1998, College Station, Texas, U.S.), joint recipient, with Odd Hassel of Norway, of the 1969 Nobel Prize for Chemistry for his work on “conformational analysis,” the study of the three-dimensional geometric structure of complex molecules, now an essential part of organic chemistry.

Education and early career

The son and grandson of successful carpenters, Barton was able to attend a good private school. Rather than join his father’s wood business after graduation, he chose to pursue higher education. After one year at Gillingham Technical College, Barton entered Imperial College of Science and Technology in London, where he developed what became a lifelong interest in the chemistry of natural products. Barton earned both his baccalaureate and doctoral degrees from Imperial College, in 1940 and 1942, respectively. Upon completing his doctoral research, Barton spent much of the remainder of World War II investigating invisible inks for military intelligence purposes. After a year working for the chemical industry in Birmingham, he joined the faculty of Imperial College in 1945, first as an assistant lecturer and later as a research fellow. Although the college did not offer him a position in organic chemistry, he was able to teach physical and inorganic chemistry there for four years while conducting research in his field of choice, organic chemistry. Spending time in all of these areas of chemistry helped him better appreciate the value of these interrelated disciplines.

Conformational analysis

In 1949 Barton took up a one-year visiting professorship at Harvard University that proved crucial to his intellectual and professional development. At that time he formed what became a lifelong friendship and collaboration with R.B. Woodward, and he began his seminal work on conformational analysis. Barton’s four-page “The Conformation of the Steroid Nucleus” (1950) immediately caught the attention of the scientific community, particularly organic chemists. The paper’s most immediate impact was seen in the way it provided a theoretical foundation for considerable experimental work in the field of steroid structure and synthesis. Barton’s work unified many of the diverse findings about the chemical and biological behaviour of steroids that had been uncovered during the first half of the 20th century, and it was for this work that Barton received the Nobel Prize in 1969. Returning to London in 1950, Barton took up a position at Birkbeck College, University of London. There he taught organic chemistry and pursued his research on the structure and synthesis of steroids. During this time he and Woodward completed their synthesis of lanosterol, a key intermediate in the biosynthesis of steroids.
After serving a brief period as a professor of chemistry at the University of Glasgow from 1955 to 1957, Barton returned to Imperial College where he remained for 20 years. At Imperial College he introduced a number of pedagogic innovations to complement his lectures, including seminars devoted to problem solving and a tutorial system. Barton, driven by the aesthetics of his work as well as by his own intellectual curiosity, highly valued doing useful things. The posing and solving of problems were special joys ; particularly difficult problems and elegant, efficient solutions made the task all the more enjoyable. Barton was happiest when all these ideals coalesced into one project, as they did with his work on the synthesis of aldosterone, a steroid hormone that controls the balance of electrolytes in the body.
In 1958 Barton collaborated on aldosterone with the Schering Corporation at its Research Institute for Medicine and Chemistry in Cambridge, Massachusetts. He discovered what is now known as the Barton reaction, a photochemical process that provided an easier means of synthesizing aldosterone. The project was a tremendous success, and Barton maintained a consulting relationship with Schering for the next 40 years. Barton’s scientific work flourished, too, as he successfully expanded his research agenda in the chemistry of radicals and photochemistry. He made significant and lasting contributions in all the areas of chemistry he explored, and he was knighted in 1972.

Later career

Although Barton officially retired twice, his final two decades were quite active and productive. A year before retiring from Imperial College, he was appointed director of research at the Institute of Organic Chemistry’s National Centre for Scientific Research in Gif-sur-Yvette, France, a position he held from 1977 to 1985. Ever pursuing the useful and the elegant, Barton devoted much of his energy during these years, in both France and the United States, to the development of new synthetic methods through the use of free radicals. He later viewed this pursuit as his true mission as a chemist. After reaching the mandatory retirement age in France in 1986, he accepted a distinguished professorship at Texas A&M University, which he held until his death.

Although Barton is most often remembered for his Nobel Prize-winning work on conformational analysis, he made considerable contributions to the art and science of organic chemistry. An outgoing scientist, Barton regularly traveled, accepted many lectureships and visiting professorships, and often worked as an industrial consultant. He adamantly believed in the sharing of knowledge and the importance of exposing one’s ideas to critical review.

Leo B. Slater

Additional Reading

Derek H.R. Barton and Shyamal I. Parekh, Half a Century of Free Radical Chemistry (1993), provides considerable detail about Barton’s work with free radicals. Derek H.R. Barton, Some Recollections of Gap Jumping (1991), reveals much about his career development. See also Laylin K. James (ed.), Nobel Laureates in Chemistry, 1901–1992 (1993), for both biographical and scientific information together with a brief bibliography of Barton’s writings.


Obituary : Professor Sir Derek Barton

William B Motherwell

Wednesday 25 March 1998

The Nobel Laureate Sir Derek Barton’s published scientific works in organic chemistry spanned 58 years and ranged over vast areas of the subject. He was one of the greatest chemists of this century.
Unlike most scientists who prefer to remain as specialists, Barton had a mastery of both physical and organic chemistry and a breadth of interests which enabled him to turn to new fields, moving between topics, using the information gained from one study and then applying it to another, and then returning with more new ideas to the first. The areas which he left behind were always, of course, well ploughed by others.
He considered originality to be the most important quality. His advice to younger scientists was simply stated : "If you know, in the academic world, how to do a reaction you should not do it. You should only work on reactions that are potentially important and that you do not know how to do."
Barton was educated at Tonbridge School in Kent, and, after deciding that he did not want to follow his father into the family carpentry business, he enrolled to read Chemistry at Imperial College, London, because "the fees were higher and thereforeit had to be better". He was awarded the top first class honours BSc in 1940 and completed his PhD studies some two years later with Professor Sir Ian Heilbron. From 1942 to 1944, he was employed in secret wartime research and liked to hint that he developed a new range of invisible inks for use on human skin.
He was married in 1944 to Jeanne Wilkins and, after one year in the chemical industry with Albright and Wilson in Birmingham, he returned to Imperial College as assistant lecturer. To his dismay, he was required to teach, not as an organic chemist but in the more mathematical realms of physical chemistry. This was soon to prove a blessing in disguise when, in 1948, during the tenure of an ICI Research Fellowship, he published calculations on the preferred three-dimensional shape of an organic molecule.
His critical moment of insight came in the following year when he was a visiting lecturer at Harvard and attended a seminar in Professor Louis Fieser’s group where discussions centred around unusual reactions of steroids. He disagreed with the conventional explanations, and recognised, because of his calculations, that there was an "obvious" relationship between the preferred shape of a molecule and its reactivity. His key paper on the subject, which came to be known as Conformational Analysis, was published in 1950 and led directly to the 1969 Nobel Prize for Chemistry, which he shared with the Norwegian physical chemist Odd Hassel.
On his return to the UK he moved to Birkbeck College, London, first as Reader and then, at the early age of 35, as Professor. In 1955, Barton was invited to become Regius Professor of Chemistry at Glasgow University, where space was at a premium andhe was installed in a glass partitioned office within his own research laboratory. From this excellent viewpoint, frequent and silent forays were made into the surrounding laboratory to startle his co- workers and enquire after the results of "our latest experiment".
The stay in Glasgow lasted only 18 months, however. The sudden death of Professor A.E. Braude precipitated his recall to his Alma Mater, and he was then to remain at Imperial College, ultimately as Hofmann Professor, for the next 20 years.
During the Fifties, he was also preoccupied with elucidating the detailed structure of natural products of plant and animal origin but he recognised the advent of new spectroscopic machines would soon make this a routine pursuit. He began to pursue "The Invention of New Chemical Reactions" as his intellectual challenge. These were to prove his preoccupation for almost another 40 years, and led to extraordinary productivity.
His original approach can be illustrated by a reaction now known as the Barton Nitrite Photolysis. It was unusual since it used light as the energy source at a time when most organic chemists were using heat, and also remarkable because species called "free radicals" were involved, while the traditional organic synthesis of the day was firmly rooted in the use of positively and negatively charged intermediates. Most importantly, it provided a method for preparing the steroid aldosterone at a time
when the world supply from natural sources was only a few milligrams. The power of the new reaction was demonstrated at a lecture when Barton produced a bottle containing 60 grams of the steroid.
Free radicals were also used in a theory called phenolic oxidative coupling which explained how complex stuctures such as morphine could be made inside plants. His "retreat and return" philosophy can be seen again in the Barton- McCombie free radical deoxygenation (1975) which was used to modify antibiotics and in the radical reagents called Barton Esters (1983). In these "firsts" and a host of other areas such as fluorination, Vitamin D chemistry, or penicillins, Barton made major contributions
which would be the single high point in the careers of most other organic chemists.
In the summer of 1977, Barton shocked the UK scientific establishment by announcing that, since he did not wish to retire at 65, he would move to the village of Gif-sur-Yvette near Paris as Director of the Institut de Chimie des Substances Naturelles, a world-renowned centrepiece of the French CNRS research system. His selection of France was made, not only because of his love of fine French wines and cheeses, but also for his French second wife, Christiane Cognet, whom he had married in 1969.
The years in Gif were extremely creative, and he adjusted easily to the French rhythm of life. Visiting speakers at the Institut were treated to sumptuous three-hour lunches prepared by Christiane, beginning with champagnes and ending with Sauternes. His co-workers invited to lunch could have problems when they returned to the lab at 3.30pm for another five hours’ work.
This period also saw Barton begin to tackle his last great scientific challenge - the oxidation of saturated hydrocarbons. The problem here lies in converting basic petroleum products such as methane into feedstock for the fine chemical industry. Yet again, drawing inspiration from the chemical reactions occurring in nature, and thinking about the atmosphere of a primordial earth, he invented the Gif Oxidation, a combination of air, iron powder, hydrogen sulphide, vinegar and a dash of pyridine - and it worked.
In 1986, at the age of 68, and faced again by the prospect of an unwanted retirement, he made his final move and accepted an invitation to become Distinguished Professor of Chemistry at Texas A and M University, where he relished the competition of the American funding system.
Following the death of his wife Christiane in 1992, he married Judith Cobb and, from the home provided by Judy, and the two dogs on whom he doted, he continued to travel on the international science scene at a pace which would be the envy of those only half his age.
Derek Barton had a complex personality. The public persona presented in scientific meetings was of a rather forbidding figure, and his scientific rigour meant that he was always the first to ask probing questions after a lecture. Though he mellowed over the years, many of his colleagues were somewhat in awe of him, and found it hard to live up to his demanding standards, so that research discussions were often conducted on a polite and formal level.
In social gatherings, too, he was a little uncomfortable and keen to escape. To those who knew him well however, and with whom he could relax, an entirely different personality was revealed. At these times, he had a great sense of fun, loving to tell stories of people and places and revealing a surprisingly catholic range of interests in unsuspected areas such as literature and music. He was intensely proud of the world-wide family of his former colleagues and, as a "godfather", he always wishedto help them.
Barton liked to set himself new targets - and to meet them. One of these, made over 10 years ago, was to publish 1,000 research papers before the age of 80, and in this, he surpassed his goal : a remarkable achievement from a remarkable man.
Derek Harold Richard Barton, chemist : born Gravesend, Kent 8 September 1918 ; Assistant Lecturer, Department of Chemistry, Imperial College 1945- 46, ICI Research Fellow 1946-49 ; Reader in Organic Chemistry, Birkbeck College 1950-53, Professor of Organic Chemistry 1953-55 ; FRS 1954 ; Regius Professor of Chemistry, Glasgow University 1955-57 ; FRSE 1956 ; Professor of Organic Chemistry, Imperial College 1957-70, Hofmann Professor of Organic Chemistry 1970-78, Emeritus Professor of Organic Chemistry, London University 1978-98 ; Nobel Prize for Chemistry (jointly with Odd Hassel) 1969 ; Kt 1972 ; Director, Institut de Chimie des Substances Naturelles, CNRS 1977-85 ; Distinguished Professor of Chemistry, Texas A and M University 1986-95, Dow Distinguished Professor of Chemical Invention 1995-98 ; married 1944 Jeanne Wilkins (one son ; marriage dissolved), 1969 Christiane Cognet (died 1992), 1993 Judith Cobb ; died College Station, Texas 16 March 1998.


Molecules 1998, 3, 132-134

Obituary : Professor Sir Derek H. R. Barton (1918-1998)

Shu-Kun Lin

Received : 19 March 1998 / Published : 20 March 1998

Professor Sir Derek H. R. Barton
(8 September 1918 - 16 March 1998)

With great sadness I just learned that Professor Sir Derek H. R. Barton died in the evening of 16 March 1998, at age 80.

Professor Barton had been very supportive to our electronic journal, Molecules (http://www.mdpi.org/molecules) and served on the Editorial Board from the beginning. He also immediately accepted my invitation to be a member of the International Scientific Advisory Committee of the related conference ECSOC-1 as well as ECSOC-2(The 2nd International Electronic Conference on Synthetic Organic Chemistry, http://www.mdpi.org/ ecsoc-2.htm). He served on the editorial boards of numerous other chemistry journals also. He was the chairman and one of the founding editors of the famous Tetrahedron publications.

Even in recent years, at high age, Professor Barton had been very active in the chemistry community.

He had been invited to many symposia, chemistry seminars, colloquium series, and conference lectures, even in recent years. I have attended his lecture entitled "How to win a Nobel Prize" twice, the first time was at the University of Louisville, USA in 1988, and it was always very stimulating and full of fascinating details.

He had been active in scientific research even in very recent years as we can find his frequent publication of research papers [1] and always ready to embrace new things such as Internet application in chemistry. We exchanged several e-mails recently. It is a shock that he suddenly passed away.

Derek Harold Richard Barton [2] was born on 8 September 1918, son of William Thomas and Maude Henrietta Barton. He obtained his B. Sc. Hons. (1st Class) in 1940 and Ph. D. (Organic Chemistry) in 1942, from University of London, Imperial College. After two years in military intelligence and one in industry, he returned to Imperial College to teach inorganic and physical chemistry. He then began an academic odyssey with stops at Harvard, Birkbeck College, and Glasgow.

In 1950, in a brief paper in Experienta entitled "The Conformation of the Steroid Nucleus", Professor Barton showed that organic molecules in general and steroid molecules in particular could be assigned a preferred conformation based upon results accumulated by chemical physicists, in particular by Odd Hassel. Thus he established the concept of conformational analysis. He returned to Imperial College as professor of organic chemistry in 1957.

In 1969 he shared the Nobel Prize in Chemistry for his work on conformational analysis.

Professor Barton was knighted by Queen Elizabeth II in 1972 but, by his choice, was known as Sir Derek only in England.

In 1978 he became the Director of the Natural Products Institute at Gif-sur-Yvette in France, and in 1986 he became Distinguished Professor at Texas A&M and held this position for 12 years until his death.

Besides the Nobel Prize, Professor Barton won many honours. More recently, he won ACS Creative Work in Synthetic Chemistry Award in 1989 and ACS Priestley Award in 1995. He was chosen as one of several most influential chemists in the past 75 years of chemical research, by Chemical & Engineering News [3].

Professor Barton has earned his place in chemical tradition the old-fashioned way, with hard work and by inventing reactions. Aside from fathering conformational analysis, his name is associated with at least five organic reactions [4] :

Barton nitrite photolysis - the long range functionalization of alcohols via nitriles leading to gamma-hydroxy oximes ;

Barton deamination - free radical deamination of primary amines via isocyanides ;

Barton decarboxylation - decarboxylation of a mixed anhydride (thiohydroxamic-carboxylic) and interception of the radicals as a sulfide, selenide or bromo derivative ;

Barton-Kellogg olefination - olefin synthesis from hydrazones and thioketones via 1,3,4-thiadiazolines ;

Barton-McCombie deoxygenation - of secondary alcohols to hydrocarbons via xanthates ;

His recent research interests were the invention of new chemical reactions, the functionalization of unactivated molecules, and the partial synthesis of natural products [4]. His most recent interests can be found at his Website [1].

Professor Barton was first married to Jeanne Kate Wilkins but this marriage was later dissolved. He married again to Professor Christiane Cognet who died in 1994. He has one son, W. G. L. Barton, by his first marriage. Professor Barton is survived by his third wife, Judy Cobb Barton ; a son, William, who lives in England, and three grand children [5].

Professor Barton was not only a great scientist, he was also a very kind man, to be remembered by all of us.

Acknowledgements : I would like to thank Dr. Matthew F. Schlecht (DuPont) for his communication and English correction, Professor Emile A. Schweikert (Head, Department of Chemistry, Texas A&M University) for allowing me to use Professor Barton’s photo and George D. Merlin McCallion for bringing my attention to the New York Times Obituaries section, 19 March 1998.

References and Notes :

1. The website of Barton group at Department of Chemistry, Texas A&M University where the description of his research interests is :

"Although organic synthesis has advanced greatly in the last few decades and is nowadays a multibillion dollar industry, it is still unusual to carry out a reaction with a quantitative yield. There is, therefore, a constant need for new reactions that are more selective and give high yields of single products. Our laboratory is concerned with the invention of such reactions.

A family of high yielding radical reactions has been introduced. These are based on the radical chemistry of the thiocarbonyl group. Important applications in carbohydrate chemistry frequently have given the nearly quantitative yields required. A more recent development has associated the thiocarbonyl group with the relatively weak nitrogen-oxygen bond to provide an efficient system for the conversion of the carboxyl group into a radical. In this way, many synthetic operations can be carried out in high yields, which were not possible before. Applications in peptide chemistry, in steroids, in nucleosides and in other areas of natural products chemistry have been made.

A second interest of the laboratory is in the selective substitution of saturated hydrocarbons. This is an excellent challenge for the present generation of chemists and for Texas. An interesting new approach has been invented for converting saturated hydrocarbons to ketones smoothly at room temperature. For a 25 percent conversion, the reaction is nearly quantitative. The selectivity is unusual as secondary positions are attacked more rapidly than tertiary centres. In steroid chemistry, a one-step synthesis of progesterone from cholestenone has been achieved.

Recent advances have enabled the conversion of saturated hydrocarbons into a number of secondary derivatives, of which bromides are of significant utility."

2. For the autobiography of his early part of life, visit Website of The Nobel Foundation.

3. See the 75th Anniversary issue, Chemical & Engineering News, 12 January 1998.

4. This summary was kindly provided by Matthew F. Schlecht, DuPont Agricultural Products, Newark, DE 19714-0030, USA, tel 302-366-5760 fax 366-5738, Matthew.F.Schlecht@usa.dupont.com

5. The New York Times Obituaries section, 19 March 1998.


S. V. LEY-R.M. MYERS-BARTON

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BIOGRAPHIE

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Derek Barton Biography, life and Career Facts, Invented

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Derek Barton Biography, life and Career Facts, Invented

Biographie 1918-1998

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biographie 1918-1998

INVENTING RADICAL CHAIN REACTIONS WITH DEREK BARTON AT THE INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES

David Crich

Formerly : Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, 1L 60607-7061, USA

Institut de Chimie des Substances Naturelles, C. N. R. S., 91198 Gif-Sur-Yvette, France

I came to know and work with Derek Barton through an entirely fortuitous set of circumstances which began when I went to the University of Surrey in 1977 to read chemistry with a minor in French. This was a so-called sandwich course with the third of the four years supposedly being spent on an industrial placement in France. Robert Thomas, at that time a Royal Society Research Professor in the Chemistry Department at Surrey, had worked with Derek in the late 1960’s at Imperial College on the structural elucidation of fusicoccin. He arranged for me to spend my "industrial year" at the ICSN, on the CNRS’s beautiful Gif-sur-Yvette campus. Thus it was that I arrived in the Prof’s office in the late summer of 1979, having just turned twenty and with only two years of an undergraduate degree under my belt. Monsieur Barton, as I was instructed to address him, wasted no time in getting down to business. He rapidly ascertained that I had a place to stay and, in his own words, that most important of items in Gif : a canteen card. He then told me that I would conduct my research in Dr. René Beugelmans’ laboratory, before going on to outline my project and to send me off to the library with instructions to read the subject up. The aim of the project was to determine the effect (none as it turned out) of steric hindrance toward electron transfer from dissolving metals to thiocarbamate esters. From my own perspective being in Rene’s lab worked out well as I saw Derek in a very small group every week and also got to learn a lot about the SRN1 reaction from the Beugelmans group. Noteworthy was the fact that even though I was only an undergraduate and not in his main group, Derek spared me the same amount of time every week as he did his other students, which was very much appreciated. At the end of my year, on the day of my departure, I took Derek my lab books and samples. He chastised me for not having them in the obligatory blue biscuit tin, then offered me a fellowship to return when I finished my degree and do my doctoral degree under him ! I didn’t hesitate and not much more than a year later I was back "à l’Institut" this time in his main group sharing a lab with Sam Zard and others and working with the wise day to day counsel of Willie Motherwell.

My new projects still had to do with electron transfer to thiocarbonyl esters with a view to finding a replacement for tin hydride in the Barton-McCombie deoxygenation reaction, something of a cause celebre for free radical chemists. This didn’t fare too well and after a time I was asked to examine the free radical chemistry of esters of thiohydroxamic acids, especially their reactions with tin hydride, in order to establish a simple radical decarboxylation reaction. Some preliminary work in the area had been done by Didier Villemin with an acyclic thiohydroxamic acid. This acid had to be prepared and, while the preparation was not overly difficult, it and the compound itself were certainly malodorous. I therefore hunted around for other thiohydroxamic acids and came across N-hydroxy-2-pyridinethione in a review by Waiter and Schaumann. This compound was easy to prepare, was nicely crystalline and odorless. I made and used significant quantities of it before Martial Thomas, the group technician, discovered that it was sold by Aldrich and Fluka, albeit under a misleading name. The chemistry worked very nicely and I was fortunate enough to discover that all kinds of radicals, as well as the tributylstannyl radical, added to the thiocarbonyl sulfur in the desired manner, which gave the chemistry considerably more breadth than had been originally anticipated. However, the best replacement for tin hydride was tertbutyl thiol, a very malodorous and volatile substance. I spent many weeks doing reductive decarboxylations using this thiol and most days someone, somewhere in the ICSN, would complain about the smell. The usual mechanism for such remonstrations was to tell M. Tchakotine, the régisseur or building manager, who would then inform the Prof.. As I was the only one working on the project, it was obvious where the blame lay and every week in the group meeting I would receive a mild admonishment to which I would reply that I was trying my best. There came a time when Derek must have tired of being interrupted by M. Tchakotine everyday and said he would come to the lab the next time the problem arose to investigate for himself. In due course Tchakotine came into our lab complaining of the smell and gleefully said he was going to fetch the Prof.. We threw open the windows, immediately, but there was still a strong smell of thiols in the air when Derek strode in a few minutes later. He made a show of sniffing the air before turning round and saying "What smell ? I can’t smell anything". We never had a complaint from within the ICSN again. The Prof did, however, receive a written complaint from the CNRS headquarters, who had been sent a letter by residents from an adjacent apartment complex. This was more serious. A meeting with Pierre Potier and Gerard Swierscki, the head administrator, was convened at which we discussed potential solutions to the problem. These included dropping the project (out of the question, synthesizing non-volatile thiols, and the making of all kinds of elaborate traps. After half an hour the blackboard was full of ideas and Derek indicated that the meeting was at an end. As we were leaving it was pointed out that we had a lot of ideas but hadn’t taken a decision, to which Derek replied that he was sure David would do his best ! Eventually, I did synthesize the considerably less offensive 3- ethylpentane-3-thiol but, as the preparation involved bubbling hydrogen sulfide through sulfuric acid solutions of the corresponding alcohol on a large scale, the cure was as bad as the cold. Several years later Brian Roberts at University College London discovered tert-dodecane thiol, an isomeric mixture sold cheaply by Aldrich, and an ideal solution to this problem.

Writing papers with Derek was an exercise in efficiency. It happened more than once that we decided late in the afternoon that enough exciting results were on hand for a manuscript to be written and that it would be good if I could bring it to him the next morning. Being as eager as he to see the work in print I would manage to do this. Then, sometime in the course of the day he would send for me and, if he agreed with the science, a few perfunctory changes would be made before the secretary was instructed to type it up and send it out. This rapid, efficient protocol was even followed with forbidden digressions. On one occasion I made what I considered to be an interesting observation and proposed in the group meeting to follow it up, but was told to focus on my main project and not get distracted. A month or so later, having spent several Sunday afternoons looking into this chemistry, I presented a table of results in the weekly meeting and, true to form, 1 was very shortly writing up a manuscript for submission to Tetrahedron where it appeared in due course. Presumably, Derek appreciated the fact that he wasn’t the only one to find chemistry more interesting than spare time.
Being a conscientious student and keeping up with the literature was fraught with danger and was not for the faint hearted. In order to visit the washroom, or indeed go anywhere from his office, Derek had to pass through the library. As such, too avid readers of the latest journals were often invited to accompany him back to the office for a discussion of the latest results These impromptu meetings were true learning experiences from which one always came away enriched and, of course, with more experiments to carry out.

Derek enjoyed nothing more than a challenge, which could be challenging for his coworkers. Athel Beckwith published an alternative mechanism to the one favored in Gif for the Barton-McCombie deoxygenation reaction in a late May 1984 issue of Chemical Communications. Within hours of the journal being delivered r was instructed to devise a method to differentiate between the two mechanisms and, hopefully, confirm the original proposal. This could have been fun were it not for the fact that the proiect had to be finished within three weeks so that Derek could surprise Athel with the results at the upcoming EUCHEM conference on Free Radicals in St. Andrews, at which both were to lecture. Some hard thinking and very long days resulted in several systems, all of which strongly supported the Bartonian mechanism but none proved it conclusively. The Sunday morning of Derek’s l1ight to the meeting saw both of us at my desk in the lab studying what ultimately would turn out to be the most interesting result in terms of subsequent developments. This was my observation that tin hydride appeared to cleave the S-alkyl and not the O-alkyl bond in O-cholestanyl S-isopropyl dithiocarbonate. My instructions that morning were to prove this, which was duly done, and telex the results to St. Andrews before the seminar. Athel was only half convinced by the evidence and a new postdoc in the Barton group subsequently had to work on the project for a whole year before he was persuaded to hand over the Australian dollar Derek had bet with him in St. Andrews. It was not until several years later that Mario Bachi, of the Weizmann Institute, carried out the definitive experiment which settled the matter once and for all in favor of the original mechanism.
The time came for me to graduate. Derek wanted me to join the CNRS and remain with him in Gif but the CNRS thought otherwise, and so it was that one Saturday afternoon we were discussing my prospects and I suggested that a postdoc in Japan would be interesting. Derek agreed and volunteered to help but asked that I wait a week before acting. The next Saturday I found that he had been busy conspiring with Pierre Potier to find me a CNRS sponsored postdoctoral fellowship to remain in Cif. Thus, the CNRS got to keep me for a year anyway, simply at a significantly higher salary. In collaboration with Yolande Hervé and Josianne Thierry we worked on the application of the decarboxylation to amino acids and synthesized L-vinylglycine. Derek was similarly persuasive when it came time for me to seek an academic position in the UK. I announced my intention to apply for all openings but he felt that only a few were appropriate. It is sobering to note that the one position he brought to my attention, was the only one for which r was interviewed and the one for which I was eventually selected. Years after I left Gif to take up my independent career and, indeed, right up to the end, it was easy to discern his hand behind the scenes steering opportunities of one kind or another in my direction.

Socializing with Derek was always entertaining. On one occasion, not atypical of my experiences, I was invited, along with the Geros and the Zards, to a dinner hosted by Derek’s excellent secretary Suchen Fan, and her husband Gerard, to celebrate the Chinese New Year. Derek and Christiane arrived, and Derek made his way around the room shaking everyone’s hand until he came to me at the end, when he pointedly declared that Englishmen didn’t shake hands among friends. He was obviously in a playful mood and continued in that theme all evening. He decided that I didn’t have much experience with Chinese food and that I should sit next to him and be coached. This mainly involved his serving me with food and drink, all of which was excellent, and ensuring that I finished up everything in sight throughout the evening. Giant shrimps formed the highlight of the dinner. Suchen declared that these were too unwieldy for chop sticks, and set the example by using her hands. Derek, challenged, countered that chopsticks were the proper implement and that he would use them, and so would David. This we proceeded to do until all had been consumed, much to the amusement of all present and even more to the detriment of the Fans’ tablecloth.

Studying under Barton was not easy. He set high standards and expected them to be met. However, once his respect was gained he was an excellent, supportive and loyal mentor. In my own case my interactions with him increased considerably after the departure of Willie Motherwell for Imperial College and it was then that I really came to know and appreciate him to the fullest extent. Perhaps not too surprising in someone who had published around nine hundred papers at the time, Barton never ceased to amaze and inspire me with the breadth of his knowledge and his instant recall of disparate yet relevant facts , either from decades ago or from the most recent journals. Of course it was this very breadth of knowledge and ability for lateral thinking that underpinned his passion for "gap jumping" and enabled him to make such a range of immensely important contributions to organic chemistry over so many years.

Derek Barton changed the face of organic chemistry in the 20th century with his introduction of conformational analysis and, through his nitrite photolysis and deoxygenation reactions with their applications in natural products, did much to ignite and then fuel the continuing explosion of preparative free radical chemistry. The picture I have tried to paint here is one also of the caring and very supportive human being with whom it was my great privilege to be associated and to have known for the best part of twenty years. His memory and example will always live with me.


SOME PERSONAL RECOLLECTIONS OF SIR DEREK BARTON FRS - A GENTLEMAN, A SCHOLAR, AND A VERY HUMAN BEING

William B. Motherwell

Formerly : Alexander Williamson Professor of Chemistry.
Christopher Ingold Laboratories.
University College London, 20 Gordon Street, London WCIH OAl, UK
Department of Chemistry University College WC1H OAJ London.

Even although all comparisons are relative, I have always felt that it was highly appropriate that my own association with "Prof" began at Imperial College on April Fool’s Day, 1975. Little did I know that we were to be together for a further eight years, and that I would be able to witness, and also to contribute, albeit in a minor way, to the evolution of a segment of the Bartonian Legacy.

In the beginning, I was exposed to the intense atmosphere in the Imperial College Laboratories at that time, and, in common with many generations of coworkers, to the ritual of the weekly research meeting with its attendant cross examination conducted in a large cloud of cigar smoke. Such cameo snapshots will also include the large mugs of tea which accompanied "The Old Man" on his silent forays into the Hofmann Laboratory to inquire after the results of "our latest experiment," and will no doubt be described by many of the contributors to this volume.

My own first experiments centered around the proposed reaction of a xanthate ester with iodine azide and, since the conversion to a chloride with iodine monochloride had already been successfully demonstrated within the group, this was predicted to be a new and straightforward method for the introduction of azide functionality.

Several explosions later however, when I reported my unsuccessful efforts to DHRB, he paused for a moment, and then said "Well, if you have tried IN3, why don’t we consider NI3". I must have looked shocked, for he then took the time to explain that it was not such an unreasonable proposition and reaction could occur either via an electrophilic or a free radical mechanism. Nevertheless, I also concluded that he had a sense of humour. Life at Imperial College certainly began with a bang !

In the summer of 1977, DHRB surprised the UK chemical community by announcing that, since he did not wish to retire at the age of 65, he was going to take up a new post as Director of the Institut de Chimie des Substances Naturelles, a justifiably renowned centerpiece of the French CNRS research system which was located in the beautiful village of Gif-sur-Yvette near Paris. While additional reasons for the move were also stated to involve his hatred of the British taxation system and his well known love of French wines and cheeses, the most compelling reason was of course his French wife, Christiane, whom he had married in 1969. For my own part, as his only colleague from Imperial College to be offered a permanent post in France, it was to prove a unique opportunity. Thus, some seven days after my own marriage in September 1977, our car of course being suitably equipped with ’Imperial’ rotavapors and other essential glassware, we crossed the English Channel.

From a scientific standpoint, the six years which we spent together in Gif were to prove a period of delightful creativity in terms of "The Invention of New Reactions". In particular, one of the most exciting aspects was that while the research philosophy remained the same, the move to France seemed to provide a blank page for entirely new areas of discovery. It was during this time that, inter alia, the use of organobismuth reagents for arylation, the free radical reactions of acylthiohydroxamates (Barton Esters), and the Gif oxidation of saturated hydrocarbons were all introduced to the chemical literature.

To my initial surprise, DHRB adjusted very easily to the French rhythm of life, and the daily work in the labs, while equally productive, was conducted in a much lighter vein. It is a measure of his personal integrity that while in France, our research discussions within the various groups were always conducted in French, even when on some occasions we did not have a single French representative present. Many new words and phrases such as "obvieusement", (évidemment) "hareng-rouge" (red herring) and "elephant-blanc" (white elephant) were introduced into the French language at this time. A very apt comparison with the I.C. days can be made by relating the tale of Madame X, a petite and very beautiful French blond. One day, on approaching the blackboard to present her results for "Le meeting", she carefully selected her piece of chalk, paused, pouted, declared that she had not done anything significant that week, and then returned to her seat. A very quiet "Merci, madame" then followed from DHRB. Afterwards, during our one to one recapitulation of research progress, I fully expected to be criticised for my failure to instill sufficient productivity. When we came to discuss the progress of Madame X however, the single comment made was "Hasn’t she got the most beautiful blue eyes you’ve ever seen ?" The French rhythm was also apparent when visiting speakers at the Institute were treated to sumptuous three course lunches prepared by Christiane beginning with Champagnes and ending with Sauternes. One such occasion was particularly memorable when an eminent visiting Bartonian selected a piece of goat’s cheese wrapped in straw and then proceeded over a period of several minutes, and with some evident discomfort, to swallow it. Conversation continued quietly during this time and the only hint given by Prof that he had noticed was a wicked little gleam in the eye. Eventually however he capitulated, saying that the digestion of straw was unnecessary. As may be imagined, it was only my wife Robyn and I, who had some difficulty in continuing to work for another five hours when we returned to the lab around 3.30 in the afternoon ! During these times, it was evident that DHRB had a great sense of fun, loving to tell stories of people and places, and to reveal a surprisingly catholic range of interests, many of them in unsuspected areas such as music and literature.

For most scientists, and even for many of his colleagues and coworkers who always remained in awe of him, the public persona of DHRB was of a rather forbidding scientific figure who was always the first to ask probing questions at the end of any lecture, and of a man who was clearly a little uncomfortable and keen to escape from more social gatherings. Hopefully, some of the tales told above will go someway towards redressing the balance, although they form only a tiny fragment of what must more properly remain as my own personal storehouse of treasured memories.
On a more serious note, there is absolutely no question that DHRB wished to be remembered for all time and that the concept of ’fame’ was a very dominant ’force motrice’ throughout his career. Those who have read ’A Mathematician’s Apology’ by G. H. Hardy can readily understand this inner drive and will also recognise that, in Prof, the necessary interwoven threads of intellectual curiosity, professional rigor, and ambition were all supplied in full measure and combined to create his enormous scientific legacy. He was always obsessed by originality and creativity in scientific work and considered that this was the most important pursuit. Consequently, his advice to younger scientists was simply stated ; " ... if you know, in the academic world, how to do a reaction you should not do it. You should only work on reactions that are potentially important and that you do not know how to do". DHRB was never a scientist who dwelt in the past but always knew when to move on and to revel in the latest results from experiments at the bench. In all of the time that I was with him, he never drew a steroid in three dimensions ! In every research area however, as every former colleague knows, scrupulous characterisation and the inevitable blank experiments were always the order of the day, and this scientific rigour applied to thought as well as to new compounds and reactions. The third thread of ambition, which, to some extent, revealed that he had always to prove himself to himself was also present. Even many years after the Nobel Prize he continued to work long hours and always remained an intensely competitive individual. Some of the targets which he set himself viz to have more Honorary Doctorates than Lord Todd or to publish over one thousand papers by the age of eighty could seem almost trivial, but they were real to him, and he continued to achieve them. On one occasion he explained to me that if he had not chosen Organic Chemistry, then he would have elected to become an eminent composer, going on to add that while the basic rules and theory of notation were there for everyone, only famous composers could develop their own characteristic signature through exercising their individual originality. Over the years, even after I had returned from Gif to London, we continued to meet on regular occasions throughout the year, such as our joint consulting sessions with Quest International or at the annual meeting of the Tetrahedron Executive Board of Editors. During this most recent period, he also found time to describe his own career in books such as ’Recollections in Gap Jumping’. When I teased him and said that some of his tales of invention might involve minor gaps in recollection, he laughed and said that it was also very important to preserve his mystique for the future. He need never have worried, his scientific legacy, as one of perhaps only two Organic Chemists this Century to merit adjectival status is entirely secure.
Perhaps the final element of the Bartonian legacy must lie in the worldwide family of his former colleagues who, irrespective of the time and place where they worked with him, are united under his name. He was always intensely proud of their own achievements and as a ’Godfather’ always worked actively, and often without their knowledge, to help them.
The world of Organic Chemistry will certainly remember Sir Derek Barton as an intellectual giant of the 20th Century, but as a Bartonian, I will always preserve my memories of him as a very human being and as a friend.


BASKING IN THE SHADOW OF A GREAT CHEMIST : HAPPY TIMES WITH SIR DEREK BARTON

Samir Z. Zard

Formerly : Institut de Chimie des Substances Naturelles, C. N. R. S., 91198 Gif-Sur-Yvette, France
Laboratoire de Synthese Organique associé au C. N. R. S., Ecole Polytechnique, 91128 Palaiseau, France

The recollections recorded in these few pages are mostly of happy moments shared with a great man. I knew Sir Derek Barton for more than 20 years and his influence on both my professional career and private life has been enormous.

1 am of Lebanese extraction, born in Nigeria, and chased away from the Lebanon by the civil war in 1975 (on Thursday, November 27th, to be exact ; this day remains vivid in my memory because we were taken to Beirut airport in an armoured personnel carrier !). After some tribulations in France and England for a couple of months, I eventually found my way to Imperial College. This was purely accidental. 1 had applied to other universities but none would take me in the middle of the academic year. My first contact with Professor Barton was in the second undergraduate year when he gave his usual four lectures on stereochemistry. This was normally the only contact most undergraduates ever had with "The Professor". In the following Summer, after the examinations, I received a letter from the administration telling me that 1 had been selected for the Hoffmann Prize in Organic Chemistry, which consisted of a gift of £ 2.10 for purchasing a book. Even then, this sum was insufficient to buy any decent chemistry book, so 1 decided not to do anything about it, the nominal financial reward attached to the prize had in fact not changed since its inception. I was therefore somewhat apprehensive when his secretary, Maria Serrano, came to see me a few months later - just before Christmas when we were in the midst of the third year practical course - to tell me that "The Professor" wished to see me. Many terror stories circulated about him in the department, and we had witnessed him being a little hard on a few of the invited Tuesday evening speakers. I was therefore very nervous on the way up to the famous 7th floor office. trying desperately to figure out a reasonable excuse to justify my not doing anything about the prize. In the ensuing meeting, which lasted perhaps thirty seconds (or so it seemed). Professor Barton told me that he was setting up a laboratory in the lnstitut de Chimie des Substances Naturelles at Gif-sur-Yvette, proposed that I join his group for my PhD thesis. and asked me to give my reply to his secretary in the afternoon. Nothing was said about the book but I learnt later from Maria that I could use up to £ 10 (I eventually found one for about £7 which of course I especially treasure).

The campus in Gif-sur-Yvette is a wonderful place. The CNRS owns, in addition to the various laboratories, a superb 18th century Chateau surrounded by a magnificent park and French style gardens which is used (in part) as a guest house. I spent the whole of the month of September 1978 in a tiny but lovely room in the loft before moving into more permanent lodgings. I also remember well my second meeting with Prof. (Professor Barton in France was referred to as Prof. ; Le Prof. ; or Monsieur Barton. depending on whether you worked in his group or not) now in his vast office in France. It lasted hardly longer than thirty seconds. I was given my (vague) research project and told that I would work under the direct supervision of Dr William B. Motherwell (Willie to his friends). I was also told that if I had any queries about chemistry, his office door was always open but for other matters I should see "Gerardski" (Gerard Swierczewski, the friendly and ever helpful administrative associate director of the Institute ; only a few could pronounce - let alone spell - his family name correctly !).
In the first few months of my PhD work, we reported our results on Fridays in the afternoon, first individually then as a group ; but as the group expanded, we were eventually split into three subgroups. Most of us were terrorized by the meetings in Prof.’s office. Not because he was unkind (in the eight years we overlapped in Gif, I have seen Prof. angry with a student maybe two or three times) but rather because of his commanding presence and the desire of each of us to please him. It was not uncommon for us to keep one or two good unreported results to save a week’s work marred by failure. I remember on one occasion I was so nervous I blurted out rapid and presumably incomprehensible Lebanese French, because Willie asked me to repeat my expose all over again. The meetings in his office were indeed in French. The newcomers from abroad had about a month or two of reprieve before having a go in French. It was a hilarious display of accents from all over the world. Like many Lebanese, I had a reasonably solid background in French, but Prof. would take an impish pleasure in correcting me. I would say for example "j’ai obtenu le produit désiré", he would intervene saying "pas désiré mais souhaité" ; "désiré" having another connotation in French ! Prof. was very proud of his mastery of the French language and was a keen reader of the serious Le Monde newspaper, but this did not prevent him from making a gaffe or two himself. One such instance occurred when he teased an especially nervous French PhD female student who did not realise that he was joking (which he rarely did in public). He finally said to her "je vous tire la jambe", this being a direct rendering of "1 am pulling your leg" ; all the poor girl could do was to look down at her legs with utter puzzlement.
A PhD student or a young post-doctoral collaborator expects to have a well defined project with specific targets as in a total synthesis. In Professor Barton’s group, the philosophy was somewhat different, and it took most of us some time to realize what the priorities were. In hindsight, the guiding theme was in fact a constant search for novelty and unexpected behaviour, even though certain specific problems would be continuously tackled until they yielded. In a sense, the approach was exploratory in nature but driven both by a candid curiosity, which Prof. kept until the very end, and a tenacious, conquering spirit that defined ambitious objectives to be attained. The organobismuth mediated oxidations and arylations, and the exceptionally powerful radical decarboxylation reaction using thiohydroxamate esters, are two major discoveries I was privileged to witness at close quarters. They reflect the constant interplay between bold conjectures and serendipitous findings which Prof. mastered to an amazing degree ("have we done the blank experiment - or experience blanche" was a recurring question). Perhaps I may illustrate this technique by the following chemistry story. Prof. was a consultant for Roussel-Uclaf (as it was known then) who produced cortisone and other corticosteroids starting with bile acids, and one of their problems was to find a better way to get rid of the three extra carbons in the side chain to access the pregnane skeleton.

I was thus given the project and asked to think about it, and perhaps make some propositions. A week or so later, I scribbled on the blackboard a scheme involving the intermediacy of an oxazoline. This I intended to make by a three step procedure based on the literature. What I heard was : "But this is not original. Why don’t you use boric acid ; you should get the oxazoline directly from the free carboxylic acid". This was not then a known process and I do not know how boric acid came to his mind.
And he was right. By heating a mixture of the bile acid, 2-methyl-2-amino-I-propanol, and excess boric acid in refluxing xylene, a 95 % yield of the desired oxazoline was obtained. The next step was the introduction of an unsaturation α to the isoxazoline group. He let me have a go at a halogenation-dehydrohalogenation sequence which not only was un-original but did not work very well. I think his patience in this case must have lasted about two weeks. He called me up and. after I recounted my latest unsuccessful struggles, he suggested that I try blasting this oxazoline with one of his favourite reagents : phenylseleninic anhydride. This I did with spectacular results. The reaction took five minutes and the yield of the unsaturated oxazoIine was nearly quantitative. Yet another new reaction. What Prof. did not predict was that further cooking of the mixture leads directly to the long desired ketone albeit in only 30-40% yield. A more efficient route to the ketone from the unsaturated oxazoline consisted in shifting the double bond by treatment with phosgene (or trichloroacetyl chloride) and base, followed by cleavage with ozone.
Our labs were one floor below his office and he rarely came down to see us. One evening, however, he did come in on his way home went past me towards a Portuguese student who was turning her back to him and who did not hear him arrive. He always wore crepe-soled shoes which did not make any noise on the tiled floor. He leaned over her and gently said" bonsoir". She looked up and screamed as if she had seen the devil. and of course dropped the flask she was holding. Prof. left the room as silently as he came in and his visits became even less frequent after that.

We had more chance of seeing him in the library which was just outside his office and which he had to cross to go to the men’s room. We were safe on his way out but would often risk being called into his office on his way back. One day, I saw him come out and thought it would be better to disappear into one of the library aisles before he returned. But to not avail, I soon heard his voice coming from behind, asking me about the latest results and if it would not be better for us to discuss this in his office. All in all, it was safer to stay in the lab during "his" long working hours at the Institute and go to the library when he was not around. I say his working hours at the Institute because he also had working hours at home which began very early in the morning. Early means 3:00 am. and this is no exaggeration. Many years later, he would sometimes stay with us when he visited France and I can confirm that he woke up at three in the morning and worked. We would make sure he had a good supply of oranges which he liked to have after his usual cup of tea. He always carried with him a small tea making equipment while travelling.

My thesis concerned mostly problems in steroids and, in one meeting, Prof. suggested that I read the famous book on steroids by Louis & Mary Fieser, and proposed to lend me his copy. I replied that I had already borrowed the book from the library and was avidly reading it. I said, moreover, that I had been trying unsuccessfully to get a copy for myself but that, unfortunately, the book was out of print and no second hand book shop seemed to keep it. Some months later, Prof. went on a long trip to America, as he still had links with RIMAC (Research Institute for Medicine and Chemistry) near Boston. Upon his return, I was immediately summoned into his office. I went up with terror in my heart, expecting to be scolded because the project was not progressing fast enough. But as I came in, he just grinned and handed me a plastic bag saying "this is for you". I opened it, and my eyes popped out : it contained an almost brand new copy of "The Steroids" by Fieser & Fieser. I say "almost" because the book belonged formerly to Dr. Maurice Pechet, a director at RIMAC, whose name was stamped on the inside jacket. I only got to know the real story 20 years later when I met Dr. Pechet at the Barton memorial ceremony in Texas. During his visit at RIMAC, Prof. stayed with the Pechets and, waking up at 3 am, went walking around the house and noticed, on one of the bookshelves, two copies of the book in question. He persuaded Dr. Pechet to relinquish one of them, which he brought over with him and gave to me. In retrospect, I am even more grateful because, having had occasion to travel with him, I have seen how lightly he travelled, carrying only the very strict minimum. The book on steroids weighed easily more than three pounds.

When Willie left France to take up a lectureship at Imperial College, I was promoted to one of three "lieutenants" - it took three of us to replace Willie ! I still had to do bench work, which I have always enjoyed doing, but one aspect was especially challenging and amusing. Prof. often had bets, not only with his co-workers, but also with chemists from everywhere. He would thus sometimes call the lab when he was abroad and say that so and so claims we can’t get a such and such Barton reaction (and they were many !) to work in better than 50 % yield. Since we knew he was a bad looser, we had to really do our best to make sure he would carry the day. In France these bets were usually for ten Francs or, more rarely, a bottle of wine ; he had a jar full of coins and signed bank notes from all over the world as a testimony to his victories.

Another job I had to do was writing papers, which he promptly corrected and sent to the editors. These were the days when all had to be done by hand ; word processors were just coming out and were not available in the labs. The manuscripts were typed with lightning speed by Mrs. Su Chen Fan, Prof.’s wonderful secretary, who also learned how to draw chemical structures. This saved us a lot of time ; in fact she became so good at it that she would sometimes embarrass us by spotting the odd pentavalent carbon ! One day, Prof. called me into his office and said that we had to write a review covering a lecture he had to give at a IUPAC meeting in China. He handed me two hand-written sheets and asked me to take it on from there. I dutifully copied his wide spaced text, which amounted to an introductory paragraph, and proceeded to complete the manuscript which I gave to him a fortnight or so later. As expected, he called me up the next morning and said : "your manuscript is OK, Sam ; I especially liked the introduction !"
With time, our relationship became less and less formal. He would occasionally call me to his office and ask me how the people were doing in the lab. The ensuing discussion would often last for an hour or more, with both of us in front of his large blackboard. He would make various suggestions for each of the co-workers and, normally, would go back to his desk and I would return to the lab. Sometimes, albeit not very often, he would ask me to sit down and we would chat for another while. These were moments I especially enjoyed because he would recount all kinds of stories about chemists of the past and present, the way chemistry had evolved, the fierce competition between the world’s best research groups vying to be the first to determine (by classical degradation - now made obsolete by the advent of X-ray crystallography and NMR) the structure of some natural product, and also how Sir Robert Robinson chased Bob Woodward with an umbrella in a London railway station. In these privileged meetings, I learnt a great deal of chemistry and saw his nimble, wonderfully creative mind jump all over the periodic table. The breadth of his knowledge was simply unbelievable.

Being a "lieutenant" carried other privileges. We were thus included in the guest list when he got his Legion d’Honneur and was decorated by President Mitterrand at the Elysee Palace. I think it was the only time I saw Prof. blush. More frequent, however, were invitations to his flat to have lunch with a guest speaker. These were also memorable occasions. The meals, prepared by Christiane, Prof.’s second wife, were outstandingly good, and the wine selection always superb. She would cycle to Orsay, 5 km away from Gif, just to buy the cheese from a special "fromagerie". Christiane’s gentle and mellowing influence on him was considerable : I cannot imagine Prof. taking a two hour lunch break from work were it not for her irresistible cooking. She also knew all the co-workers by their first names and would often put in a kind word for them. Christiane also insisted on taking some holidays, which Prof. almost never did in the past. He eventually accepted to spend a week or two in their flat in Antibes, in the South of France ; but he would grumble about it. In France, holidays are sacred, and he often complained that people were so tired when they returned from holidays that they needed more holidays to recover ! I sometimes had the chore of watering the plants when they were both away. Christiane’s untimely death from ovarian cancer, postponed for a while by treatment with Taxotere (at the time still an experimental drug obtained through the agency of his friend, Pierre Potier) just shattered him and all those who knew her.

In 1986, the retirement age was lowered to 65 years, and Prof., nearly 68, decided to move to Texas A&M. This was the cause of an amusing event. I was called into his office and asked if I was free on Saturday afternoon, and if I could bring my car over. I was at first puzzled by this unusual request. It turned out that, because he had always used public transport, he never needed to drive a car in France ; but in America a car is essential, and he wanted to make sure he still could drive properly. Whence the need for a test drive on my car. I had a tatty old blue Peugeot 104 at the time and I thought it would be better if I came over with my wife’s more recent and more presentable white Renault 11 - a far cry from the Jensen "Interceptor" he used to own in England. What I can say is that he drove a little too fast and too close to the curb for my liking (remember, in England they drive on the wrong side of the road) but, of course, I refrained from making any comments.

The Barton I got to know was very different from what the rumours described him to be. Of course he wanted us to work hard. Of course he was impatient with sloppy and unoriginal work (and also with pompous lecturers). But then he never asked from us more than what he asked from himself, and he always gave the example. The iron discipline he imposed upon himself was awe-striking : I recall receiving a letter from him dated on Christmas day, at a time when Christiane was critically ill in the hospital in Houston. I cannot imagine myself writing letters under such painful circumstances, but he would do it because it had to be done. Every minute counted and every minute had to be put into good use.

He was a true gentleman with a generous heart. His generosity and warmth transpired in many ways, and I have witnessed, on numerous occasions, actions showing that he really cared for the people who worked with him. In fact, many did not realize how much Prof. had done to help them because he never said anything about it. And this applied even to the less gifted members of his group. Many would be pleasantly surprised by the letters of recommendation he has written on their behalf. In my case, he wrote several of these, without my asking, and of which I learnt only many years later. Certainly my career would have been very different were it not for his discreet but no less decisive support. For my first trip to College Station, on his invitation, I had made arrangements with one of the French students who was finishing his thesis in Texas, to meet me at the airport and take me to my lodgings. When I arrived, exhausted after a long trans-Atlantic flight and an awkward connection through Dallas, I was happy to see my friend waiting for me ; but I was very deeply moved when I saw Prof. standing next to him. He had left his office and drove to the airport, just to make sure that everything was in order. This is a moment in my life I cannot ever forget.
Sometimes, Prof. helped people without himself realizing it, as this fabulous story clearly demonstrates. One of his former French students had a job in California and attended the ceremony in honour of his 80th birthday, organized by K. C. Nicolaou at The Scripps Institute. Unfortunately for her, she lost her job a few days later and had to apply for a position in other companies in the vicinity. She obtained an interview soon afterwards, but when she told the senior chemist who was interviewing her that he could contact Professor Barton for an opinion, he said that this was not necessary : he too attended the ceremony at Scripps and saw Sir Derek kiss her. That was good enough for him and he hired her on the spot ! I must hasten to add that Prof. did not do anything improper. It is common practice in France to kiss a lady acquaintance on the cheek, four times in the case of - lucky - Parisians. This event happened just before his passing away, and I do not think he got to know about it. I am sure he would have been very pleased.
Another story I heard the day after he died. Judy Barton phoned me on Tuesday, March the 17th, to tell me that Derek had a massive heart attack the previous evening and did not survive. It was lunch time in France but, with the time lag, still only five o’clock in the morning in Texas. In her tired voice, she asked me to phone up a few people in France to let them know the sad news. When I called one French colleague in the south of France, he, like myself and all the others, was filled with sorrow and grief. He said to me that when his own wife died, Monsieur Barton called him from America to offer sympathy and ask if there was anything he could do to perpetuate her memory. His wife wanted no flowers, so Monsieur Barton sent a fat cheque from Texas to a charity with which she had a long association. At the end of the painful telephone conversation, my colleague said : "c’était un seigneur". Indeed he was.

"History, with its flickering lamp, stumbles along the trail of the past, trying to reconstruct its scenes, to revive its echoes, and kindle with pale gleams the passion of former days. What is the worth of all this ? The only guide to a man is his conscience ; the only shield to his memory is the rectitude and sincerity of his actions." These are a few lines taken from Churchill’s eulogy of Neville Chamberlain. I have, in my own candid and imperfect words, tried to revive the echoes of a golden age now gone for ever : nearly a decade of direct collaboration in France and many years of correspondence and encounters on both sides of the Atlantic. The thirty seconds I spent in his office at Imperial College have completely altered my life.
But Sir Derek Barton need not fear for his memory : his numerous fundamental discoveries and inventions will secure him an eternal front seat in the history of organic chemistry, a branch of Science he has profoundly and durably changed. His rectitude, scrupulous honesty, strict fairness, the warmth of his heart, the kindness and generosity of his spirit are other aspects I also wish to keep on record.

Source : The Bartonian Legacy, A. I. Scott et P. Potier éditeurs, Imperial College Press, 2000.

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Gap jumping

SOUVENIRS DE CES MOMENTS PARTICULIERS : LES "MEETINGS"

Alex Pestana


Comment avoir le prix Nobel ?

Les bases de l’analyse conformationelle :

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Article Experientia
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Barton’s Nobel lecture

Sir Derek nous explique les rudiments de la chimie en 3D

Sources : http://www.ch.ic.ac.uk/video/barton/steroid_qt.html

et http://www.ch.ic.ac.uk/video/barton/index_qt.html


Pour son centenaire, en 1977, le Royal Institute of Chemistry a édité des timbres commémorant les prix Nobel de Chimie britanniques, dont l’un, bien sûr, était dédié à Sir Derek :





Sir Derek a lui-même publié dans "Reason and imagination : reflections on research in organic chemistry ..." une compilation d’articles qui selon lui représentaient des tournants dans sa carrière. On peut y trouver un aperçu de l’éclectisme et de l’importance de ses contributions.


Plaque commémorative à Londres, près de l’Imperial College

Source

Egalement


Derek Barton et Geoffrey Wilkinson : deux géants de l’Imperial College

Sir Derek dans son laboratoire de l’Imperial College :

Récit de Hannah Gay :

Source

IMG/mp3/hannah_gay.mp3

Récit de Willie Motherwell :

Source


La gazette du campus honore le départ en 1986 de Sir Derek à College Station, Texas, sous la plume de Pierre Potier.

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Départ de Sir Derek aux Etats-Unis

Souvenirs de Tony Barrett :

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Souvenirs d’AGM Barrett

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