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Robert Burns Woodward The Life and Achievements of Robert Burns Woodward Long Literature Seminar July 13, 2009 Erika A. Crane “The structure known, but not yet accessible by synthesis, is to the chemist what the unclimbed mountain, the uncharted sea, the untilled field, the unreached planet, are to other men. The achievement of the objective in itself cannot but thrill all chemists, who even before they know the details of the journey can apprehend from their own experience the joys and elations, the disappointments and false hopes, the obstacles overcome, the frustrations subdued, which they experienced who traversed a road to the goal. The unique challenge which chemical synthesis provides for the creative imagination and the skilled hand ensures that it will endure as long as men write books, paint pictures, and fashion things which are beautiful, or practical, or both.” “Art and Science in the Synthesis of Organic Compounds: Retrospect and Prospect,” in Pointers and Pathways in Research (Bombay:CIBA of India, 1963). Robert Burns Woodward • Graduated from MIT with his Ph.D. in chemistry at the age of 20 Woodward taught by example and captivated • A tenured professor at Harvard by the age of 29 the young... “Woodward largely taught principles and values. He showed us by • Published 196 papers before his death at age example and precept that if anything is worth 62 doing, it should be done intelligently, intensely • Received 24 honorary degrees and passionately.” • Received 26 medals & awards including the -Daniel Kemp National Medal of Science in 1964, the Nobel Prize in 1965, and he was one of the first recipients of the Arthur C. Cope Award in 1973 RBW: The Early Years • Robert Burns Woodward was born to Arthur and Margaret Woodward in Boston, Massachusetts on April 10, 1917 • In 1918, Robertʼs father, Arthur, died in the great influenza pandemic • Robertʼs mother, Margaret, remarried but was soon abandoned to raise Robert on her own Courtesy of Harvard University Archives RBW: The Early Years • Robert grew up and was educated in Quincy, Massachusetts • When Robert was 8 years old in 1925, he received his first chemistry set • By the age of 12 in 1929, Robert had completed all of the experiments in Ludwig Gattermannʼs Practical Methods of Organic Chemistry (1894) Courtesy of Harvard University Archives “I fell in love with the field [of organic synthesis] when I was a small boy and the affair is still going on.” -RBW “Opening Remarks,” in Organic Synthesis (Robert A. Welch Foundation Conference on Chemical Research, 12, 1969). Bridging into Academia: RBW at MIT • Woodward enrolled at MIT in 1933, at the age of 16 • After his freshman year, he was given his own laboratory • At the end of the first semester of his sophomore year, Robert was advised to withdrawal from college due to his neglect of his classes Courtesy of MIT Museum Bridging into Academia: RBW at MIT • Robert spent a semester as an employee of the MIT biology department • He was permitted to re-enroll in school through the good offices of James F. Norris • RBW earned a B.S. and a PhD from MIT in only four years, graduating in 1937 at the age of 20 James F. Norris, professor of organic chemistry at MIT and president of the American Chemical Society (1925-1926) Courtesy of MIT Museum Bridging into Academia: RBW at MIT “We saw we had a person who possessed a very unusual mind in our midst. We wanted to let it function at its best. If red tape which was necessary for other less brilliant students had to go, we cut it. We did for Woodward what we have done for no other student in the department. And we think he will make a name for himself in the scientific world.” -James F. Norris From the interview of James F. Norris at RBWʼs graduation by the Boston Globe 8 June 1937 James F. Norris, professor of organic chemistry at MIT and president of the American Chemical Society (1925-1926) Courtesy of MIT Museum Love & Marriage • In 1937, Robert married a high school classmate, Irja Pullman • They had two children in their 10 years together: Siiri Anne and Jean Kirsten Courtesy of Harvard University Archives A Summer at the University of Illinois Courtesy of C&EN News Professor Carl “Speed” Marvel University of Illinois (1915-1961) Courtesy of the University of Illinois • RBW spent the summer of 1937 teaching of University of Illinois Professor Roger Adams, Chemistry Department Chair, • He “managed through his intelligence and impatience to alienate University of Illinois (1926-1957) several of the leading figures of organic chemistry in the United States”. • Frank Westheimer, a colleague and friend, said he believed “that Bob failed to conceal adequately that he was much brighter than the Illinois professors.” Moving to Harvard Courtesy of the National Academy of Sciences • In fall of 1937 through 1938, Robert worked as an Research Assistant to Elmer P. Kohler • In 1938, RBW was appointed as a Junior Fellow in the Society of Fellows until 1940 • In 1941, Robert was made an official instructor of chemistry Professor Elmer P. Kohler, Harvard (1912-1938) “That marvelous institution was founded, at Harvard, by A. Lawrence Lowell, whose conviction it was that scholars should be gentleman, entirely free to follow their intellectual interests...One could read, learn, cogitate–even work, if one felt the urge–and plan the future, however unconsciously.” -RBW Address on receiving the American Chemical Societyʼs Arthur C. Cope Award in Organic Chemistry, 28 August 1973. Woodwardʼs Inspiration “From the first awakening of • Woodward was particularly drawn to the work of my interest in Friedrich August Kekule and chemistry, I Archibald Scott Cooper have found its history absorbing, and have been particularly entranced by Friedrich August Kekule the concept of bonding in the most general sense.” -RBW Address on receiving the American Chemical Societyʼs Arthur C. Cope Award in Organic Chemistry, 28 August 1973. Archibald Scott Cooper Woodwardʼs Inspiration Friedrich August Kekule Kekule structures Woodwardʼs Inspiration O OH C C O OH O2 O2 H C H O OH – H2O C O2 O OH C H C H O2 2 C O O OH C O OH tartaric acid Archibald Scott Cooper Woodwardʼs Inspiration • In 1927, at the age of 10, RBW proposed his own structure of benzene • He later realized that this was simply a 2D representation of the prism structure proposed by Albert Ladenburg 50 years prior • However it was Kekuleʼs structures that inspired Woodward to propose that benzene could be made by adding a olefin to a diene In the Nr. 1 issue of Liebigʼs Annalen for 1928 was “Synthesen in der hydroaromatischen Reine” by Otto Diels and Kurt Alder The Woodward Rules (1941-1942) • The Woodward Rules (also known as the Woodward- O Fieser rules) were proposed in 4 papers in 1941-1942 α • In his first paper, he founds that generalizations could R be made between spectra if the absorption effects of different solvents was accounted for β β • He also found that the extent of substitution at the α and β positions of a α,β-unsaturated ketone could be determined from the UV spectra absorbs in the 230-250 mμ region Woodward, R. B. Structure and absorption of α,β-unsaturated ketones, J. Am. Chem. Soc. 1941, 63, 495-498. The Woodward Rules (1941-1942) O • The first article was based solely on the experimental work of others, citing more than forty papers α R • In particular, the work by Heinz Dannenburg was pertinent to Woodwardʼs evaluation β β • His rules concentrated on numerical analysis and built support for these rules with many examples absorbs in the 230-250 mμ region Woodward, R. B. Structure and absorption of α,β-unsaturated ketones, J. Am. Chem. Soc. 1941, 63, 495-498. The Woodward Rules (1941-1942) O α • The last three papers adapted the rules to α,β- unsaturated ketones and conjugated dienes within and external to ring structures β Woodward, R. B.; Clifford, A. F. Structure and absorption spectra. II. 3-acetoxy-Δ5-(6)-norcholestene-7-carboxylic acid, J. Am. Chem. Soc. 1941, 63, 2727-2729. Woodward, R. B. Structure and absorption spectra. III. Normal conjugated dienes. J. Am. Chem. Soc. 1942, 64, 72-75. Woodward, R. B. Structure and absorption spectra. IV. Further observation of α,β-unsaturated ketones, J. Am. Chem. Soc. 1942, 64, 76-77. The Woodward Rules (1941-1942) Me C8H17 Me • Woodward provided evidence against the then- accepted structure of 3-acetoxy-6-keto-7-hydroxy-Δ4- OR chloestene O • The compound had a λmax of 230 mμ when it should be at 239 ± 5 mμ with a small intensity band at 300 mμ too R = H or COC6H5 5 • Proposed the structure of 3-acetoxy-Δ -(6)- Me norcholestene-7-carboxylic instead Me !C8H17 CO2H Woodward, R. B.; Clifford, A. F. Structure and absorption spectra. II. 3-acetoxy-Δ5-(6)-norcholestene-7-carboxylic acid, J. Am. Chem. Soc. 1941, 63, 2727-2729. The Woodward Rules (1941-1942) • In 1949, the rules were extended by Louis and Mary Fieser • UV spectroscopy was later superseded by newer structure determination techniques such as nuclear magnetic resonance spectroscopy, mass spectroscopy and X-ray crystallography • The use of physicochemical measurements in structural organic chemistry was a major landmark O O α α R β β β The elucidation of these rules demonstrated RBWʼs remarkable power of analysis and his passion for scientific order Synthesis of Quinine 1943-1944 H H HO N MeO Quinine N • Quinine was discovered by the Quechua Indians of Peru in the 17th century in the bark of cinchona trees • Jesuits recognized itʼs ability to treat malaria and sent it back to Europe • The cinchona bark was ground up in put in sweetened water to offset the bitter
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