ENGLISH ORGANIC CHEMIST 1886–1975
An acknowledged giant of twentieth-century organic chemistry, Robert Robinson authored 700 research papers that continue to influence the way organic chemists think about synthesis, natural products, and reaction mechanisms. He received many awards during his sixty-year career, including the 1947 Nobel Prize in chemistry "for his investigations on plant products of biological importance, especially the alkaloids."
Robinson was born on September 13, 1886, near Chesterfield, England. His father owned a surgical dressing factory and invented many of the machines used to produce and package such dressings. In high school Robinson excelled in mathematics and physics and hoped to become a mathematician. However, his father encouraged him to study chemistry instead, so Robinson accepted the inevitable and entered the chemistry program at the University of Manchester.
Robinson received his D.Sc. from Manchester in 1910 and lectured there for two additional years. He then accepted successive academic appointments at Sydney, Liverpool, Manchester, London, and finally Oxford University.
Today chemists use computer-driven instruments to determine the structures of unknown organic compounds. In Robinson's era, however, chemists relied less on instruments and more on degrading the compound into smaller, less complex fragments and then piecing them back together again. Using these techniques, Robinson determined the structures of complex alkaloids and worked on the antibiotic penicillin during World War II. His work on the structure of strychnine (see Figure 1) is still regarded as an outstanding example of molecular puzzle solving.
After structure comes synthesis, and modern chemists synthesize complex medicines and other important compounds using ideas originated by Robinson. But organic synthesis was in its infancy when Robinson started out, and in his stunning synthesis of tropinone (a compound related to cocaine) in 1917, he introduced a novel strategy for preparing complex organic compounds. On paper, Robinson disconnected, or broke, certain bonds in tropinone and arrived at three simpler building blocks. He then went to the laboratory, where he combined the three building blocks using
Figure 1. Strychnine.
Figure 2. Curly arrows. E+ = an electrophile (a chemical compound or group that is attracted to electrons and tends to accept them).
standard procedures and produced tropinone. This process is now called retrograde synthesis.
Because Robinson wanted to take a systematic approach to organic synthesis, he developed a set of theoretical tools to predict the outcomes of organic reactions. Many important drugs and natural products contain substituted benzene rings, so Robinson began his research by trying to predict the outcomes of substitution reactions in benzene derivatives. He and his wife, Gertrude, successfully explained one class of substitution reactions in a 1917 paper but were unable to provide a general theory.
Using ideas developed in Arthur Lapworth's 1922 paper, Robinson devised a new theory in 1924 that explained the chemistry of unsaturated systems such as benzene and 1,4-butadiene (a four-carbon chain with alternating double bonds). Using his new theory, Robinson successfully predicted the outcomes of chemical reactions in these unsaturated systems. And for the first time ever, he used curly arrows to show the distribution of electrons in conjugated systems and to predict substitution reactions in benzene analogs. Hardly a day goes by when a modern organic chemist does not use curly arrows to explain a reaction mechanism or to plan a synthetic route.
Although Robinson considered the curly arrow concept his most important contribution to knowledge, few chemists know he invented it. Most chemists attribute the discovery to Christopher Ingold. Ingold embraced Robinson's ideas and over time published so many of his own related papers that chemists tended to overlook Robinson's groundbreaking work. Robinson never forgave Ingold for taking credit for his ideas.
Robinson retired from Oxford in 1955 but remained active in the field of chemistry. In his younger days he climbed the Alps, Pyrenees, and major mountains in New Zealand and Norway. Chess was another of his passions: Robinson spent three years as president of the British Chess Federation. He died on February 8, 1975.
Sir Robert Robinson was born at Rufford, near Chesterfield, Derbyshire on September 13th, 1886, the son of William Bradbury Robinson, a surgical dressing manufacturer who invented his own machines for the production of lint, bandages, etc., and the cardboard boxes for packaging them. He was educated at the Chesterfield Grammar School, Fulneck School, near Leeds, and at Manchester University where he graduated B.Sc. in 1906 and D.Sc. in 1910.
In 1912, he was appointed the first Professor of Pure and Applied Organic Chemistry in the University of Sydney. He returned to Britain in 1915 to take the Chair in Organic Chemistry at the University of Liverpool until 1920 when he accepted an appointment as Director of Research at the British Dyestuffs Corporation. One year later, he became Professor of Chemistry at St. Andrews and in 1922 he took the Chair in Organic Chemistry at Manchester University until 1928 when he accepted a similar post in the University of London. In 1930, he was appointed Waynflete Professor of Chemistry, Oxford University, where he remained until his retirement in 1955 when he was appointed Emeritus Professor and Honorary Fellow of Magdalen College. He has been a Director of the Shell Chemical Company and a chemical consultant since 1955.
Sir Robert has been a member of over thirty Government Committees and chairman of some of them. He was a United Kingdom delegate to the first Conference of UNESCO in 1947. He was knighted in 1939 and appointed to the Order of Merit in 1949.
Robinson's extensive researches in organic chemistry have dealt not only with the structure and synthesis of many organic bodies, but also with the electrochemical mechanism of organic reactions. His interest in the chemical constitution of plant dyestuffs (anthocyanins) soon extended to another group of vegetable bodies, the alkaloids, where the whole series of his researches are remarkable for their brilliant syntheses. He contributed greatly towards the definition of the arrangement of atoms within molecules of morphine, papaverine, narcotine, etc. These discoveries led to the successful production of certain antimalarial drugs (they are reported in numerous scientific papers, mainly in the Journal of the Chemical Society).
Sir Robert, a Fellow of the Royal Institute of Chemistry and of the Royal Society was President of The Chemical Society, 1939-1941; of the Royal Society, 1945-1950; of the British Association for the Advancement of Science, 1955; and of the Society for the Chemical Industry, 1958. He is a Commandeur de la L?gion d'Honneur and holds Honorary Doctorates of over twenty British and foreign universities. He has been honoured by The Chemical Society (Longstaff, Faraday and Flintoff Medals), the Royal Society (Davy, Royal and Copley Medals) and the Swiss, American, French and German Chemical Societies; he has also been awarded the Franklin Medal of the Franklin Institute of Philadelphia, the Albert Gold Medal of the Royal Society of Arts and the Medal of Freedom (U.S. Government). Sir Robert is Corresponding Member, Honorary Fellow, Foreign Member, Associate or Correspondant of almost fifty British and foreign learned societies.
In 1962, The Chemical Society honoured Sir Robert by establishing a Robert Robinson Lectureship, to be delivered biennially in lieu of the usual Presidential Address.
In 1912 Sir Robert married Gertrude Maud Walsh, a fellow student at Manchester University. They collaborated in several fields of chemical research, notably in a survey of anthocyanins. She died in 1954; they had one son and one daughter. In 1957, he married Stearn Sylvia Hillstrom (n?e Hershey) of New York.
In his younger days, Sir Robert was a keen mountaineer, having climbed in the Alps, Pyrenees, Norway and New Zealand, and he is an ardent chess player being President of the British Chess Federation, 1950-1953. His hobbies also include photography and music
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