Biographical Memoirs Volume 54 (1983) / Chapter Skim
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Samuel Marion McElvain
Samuel Marion McElvain
Pages 220-249
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From page 221... ...
His work resulted in major contributions to the understanding of the mechanism of certain base-catalyzed reactions of esters and to the relation between structure and reactivity. It is this latter concern, together with an unusual ability to systematize these relationships, that led McEIvain to what was probably his major scientific contribution, the discovery and study of the ketene acetals, a class of substances that proved to be of considerable synthetic interest, as well as of great significance with respect to the emerging theories of chemical reactivity.
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Solomon and Eliza (Childess) McEIvain had already had five children, four of whom cTied in infancy, when their last, Samuel Marion, was born on December 9, 1897 on a farm near DuQuoin, Illinois.
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One of the then widely held mechanisms for the important CIaisen self-condensation of ethyl acetate (the "acetoacetic ester condensation") , which is shown below, illustrates the situation: O ONa ~ 1 1)
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seemed to him highly unlikely, and he showed that the "intermediate" that had been isolated was actually a mixture of ethanol and ethyl acetate! The postulated structure did, however, seem intriguing, and McEIvain set out to synthesize the real ketene acetal.
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This is shown below o R—C Cl + CH2 = C OEt OEt O O ~ R—C—CH2C—OEt+ EtCI and will serve to illustrate the general type of reaction unclergone by ketene acetals with strong electrophiles. Note that the ,`3-ketoester thus formed is accompanied only by the volatile ethyl chloride, and that the reaction represents a completely general synthesis of the very class of compounds that had attracted McElvain's early interest in an entirely different context (see above)
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By the time he started independent work as an instructor at Wisconsin, McEIvain was convinced that structures embodying relatively simple elements of the cocaine structure might show both enhancer] anesthetic activity and lowered side effects.
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One was the celebrated course in qualitative organic analysis for which he wrote a successful text The Characterization of Organic Compounds (1945; revised edition, 19531. Many first tasted in that course the thrill of discovery and acquirer!
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In one other graduate course, or rather a portion of a graduate course that he shared with two other members of the organic staff, McEIvain must have been one of the first to teach systematically the particular way to Took at reactivity that was then called the "Electronic Theory of the English School." This referrer! to the analysis of the course of reactions based on an attempt at the rational prediction of the fate of electron pairs involvecl in bond making and breaking.
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The cheerful enthusiasm, which ~ first encountered at the Thanksgiving parties ~ mentioned, was just as apparent when I had the honor of being McEIvain Visiting Scholar in Madison in 1977. It would seem appropriate to encI this brief account of Professor McElvain's career by recording some of the more notable recognitions accorcled him: he was chairman of the Organic Division of the American Chemical Society in 1945 and 1946; on the editorial board of the Journal of the American Chemical Society, 194~1956; and he was elected to the National Academy of Sciences in 1949.
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M McEIvain Visiting Scholarship was established in 1977 and, finally, the organic laboratories in the DanielsMatthews Chemistry Building at Wisconsin were named the Samuel M
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Roland 1937 Fred Beyerstedt, Arthur Magnani 1938 Harry M Barnes, Stanford Moore, Charles W
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Raymond Mariella ~ 1 945-1 946)
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Soc., 48:2179-85. Piperidine derivatives.
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Local anesthetics derived from quinoline and isoquinoline.
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XII. Local anesthetics derived from reduction products of,l3-acetylpyridine.
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Cox. Cyclization of certain ethylenedimalonic esters by sodium ethoxide.
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Reaction of certain monosubstituted malonic esters and methylene dimalonic esters with sodium ethoxide.
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V The reaction of ketene diethylacetal with various compounds containing an active hydrogen.
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VIII. The reaction of ketene diethylacetal with a, ,8-unsaturated carbonyl compounds.
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XVII. Local anesthetics derived from substituted piperidinoalcohols.
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Chen. New piperidine derivatives as local anesthetics.
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XXIV. Preparation and properties of ketene divinyl acetal and related compounds.
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XXVII. The bromination of various ketene acetals.
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XXXIII. The addition of halogens and cyanogen compounds to methyl ketene diethyl acetal.
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Elementary Organic Chemistry.
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An Introduction to the Practice of Organic Chemistry in the Laboratory, 3d ed.
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16, 1930~. Piperidine Derivatives (local anesthetics)
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248 BIOGRAPHICAL MEMOIRS 1959 U.S. Patent 2,892,842 (June 30, 1959)
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