Biographical Memoirs Volume 67 (1995) / Chapter Skim
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Charles Roy Hauser
Charles Roy Hauser
Pages 200-219
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From page 201... ...
twenty-six articles, almost equal to the combined total for the other ten physical organic chemists whose names appear in Tarbell and Tarbell's~ extended list of prominent American physical organic chemists. Hauser's contributions to synthetic organic chemistry were recognized with the American Chemical Society's Award for Creative Work in Synthetic Organic Chemistry in 1962 and the Synthetic Organic Chemical Manufacturers Association Meclal for Creative Research in Organic Chemistry in 1967, leaving no doubt that he qualified also as an outstanding synthetic organic chemist.
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From page 202... ...
Incidentally, this latter is a process that leaves him wary of all theories, concepts or generalities that seem too well established. Interestingly, Tarbell and Tarbell,4 in their brief characterization of Hauser's contribution to organic chemistry, began by discussing his contribution to synthesis: "He developed new and useful synthetic methods and knowledge about reaction mechanisms, for which he had a real instinct." In his over 450 publications, Hauser showed wide-ranging interests, but his most memorable work was in the field of bases.
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From page 203... ...
As he grew up he had few opportunities for education but learned to support himself as a truck farmer and part-time master carpenter. He married Elizabeth Rogan, and the Hausers were living in San Jose, California, in 1900 when Charles Roy Hauser was born.
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From page 204... ...
He was one of the Duke faculty's better tennis players but abandoned the game at some time in his forties, when he took up swimming and then walking for physical recreation. His fitness program was evidently a success for it has been reported that as late as in his fifties he could walk on his hands to amuse his grandson.8 A single physical limitation, the sensitivity to light that had made him drop out of school earlier, led to self-im
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From page 205... ...
professor," Hauser became the first member of the Duke faculty to be elected to the National Academy of Sciences! In addition to his numerous research papers and chapters, Hauser had hoper} to publish a book on organic reaction mechanisms, embracing the material contained in his graduate course, but he never found a suitable coauthor.
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From page 206... ...
To most of us who knew him only professionally, the possibility of Hauser having an interest in verse or whimsy would have sounded about equally improbable, but his son has assured me that at home his father clearly liked poetry and hac3 an excellent sense of humor.6 Hauser's very limited ability to read by artificial light led not only to his previously cited inability to even scan all of the chemical literature important to his research but also to an even more limited opportunity for general reading. It is quite understanciable that this handicap, coupled with his never having been outside the United States, made him seem less sophisticated than many of his university colleagues.8 To each of his graduate students, but especially to those having problems with research or course work, Hauser could be counted on to be friendly and helpful, ready to give advice and inspiration.
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From page 207... ...
There is no doubt but that Hauser developed great skill at such organization. Not long before his death Hauser described his research interests as "fundamental organic chemical studies of mechanisms and syntheses in the fields of condensations, cyclizations, substitutions, eliminations, and molecular rearrangements."3 There is no doubt that his 450+ papers have providect us with new insights into each of these areas.
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From page 208... ...
2CHCooC2H5 (1) In his second paper of the series in 1938 Hauser enunciated what became Hauser's Rule: In all known condensations of ethyl esters a weaker base is formed than the one used to initiate the reaction.~° Hauser recognized the kinship between the ester condensation and the Perkin reaction in which, in the classic example, sodium acetate and acetic anhydride are heated together with benzaldehyde to yield, on addition of water, cinnamic acid.
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From page 209... ...
aldol intermediate could be isolated.~3 i4 An astute analysis of all results then available led Hauser and BresIow to propose a reaction mechanism (Scheme 2; B = base) that brings out the critical importance of the conjugate acid (derived from the base)
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W Kantor, Hauser found that sodium amide in liquic3 ammonia caused another type of rearrangement, affording orthmsubstitutecI benzene derivatives (TI)
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Van Eenam.~8 The Hauser rearrangement takes place by what the authors have described as an aromatic nucleophilic mechanism in which the benzene ring serves as an electron acceptor in a five-atom ring displacement (Scheme 41. The ortho-methy]
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From page 212... ...
anti, by reaction of the resulting lithium reagent with ketones, demonstrated the synthetic usefulness of the reaction. While significant as the first example of the orthmlithiation of a benzamide, it was supplanted in 1977 by a more useful metalation reaction using N,N-cliethy~benzamide (I,R = R' = Et)
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Duke Professorship by Duke University. Hauser was the recipient of three American Chemical Society awards: first, in 1957 the Florida Section Award, given to an outstanding chemist in the Southeast; then in 1962 the Herty Medal, also for an outstanding chemist in the Southeast as well as the ACS Award for Creative Work in Organic Chemistry; and, finally, in 1967 the Medal for Synthetic Organic Chemistry from the Synthetic Organic Chemical Manufacturers Association.
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From page 214... ...
Ueber die Perkin'sche Reaction: Einwirkung von Benzaldehyde auf einem Gemisch von Essigsaureanhydrid und Buttersaurem Natrium. fustus Liebig's Annalen de Chemie 227 ~ 1885)
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CHARLES ROY HAWSER 215 An evolving synthetic methodology for polysubstituted aromatics. Accounts of Chemical Research 15 ~ 1982)
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From page 216... ...
Rearrangements of benzyltrimethylammonium ion and related quaternary ammonium ions by sodium amide involving migration into the ring.
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From page 217... ...
The or/ho-substitution rearrangement versus beta-elimination of certain quaternary ammonium ions with sodium amide. Extension of the method of synthesis of vicinal alkyl aromatic derivatives.
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Factors in aldol condensations of alkyl acetates with benzophenone and reversals by sodium amide versus lithium amide. Metallic cation effects.
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