Comforth. John

Vladimir Prelog and John W. Comforth (V. P.) stereochemistry of organic molecules and reactions, (J. C.) stereochemistry of enzyme-catalyzed reactions... 

As stated by Sir John W. Comforth, "Nature, it seems, is an organic chemist having some predilection for the aldol and related condensations" [3f]. 

John Comforth Great Britain stereochemisitry of enzyme-catalyzed reactions... 

Much of Barton s work throughout his career illustrates the way in which physical organic chemistry has permeated the whole of organic chemistry.339 This is also true of the career of Vladimir Prelog (1906-1998),340 who received the 1975 Nobel Prize in Chemistry jointly with John Comforth (b. 1917) for their researches in stereochemistry. About 1950, Prelog independently put forward some of the notions that became part of conformational analysis. He too contributed a volume to the ACS series of autobiographies.341... 

The early history of stereochemistry has been explored.174 An account of stereochemistry from the mid-19th century to 1960 surveys the proposals of van t Hoff and Le Bel as well as those of later workers in the field, such as Odd Hassel and D. H. R. Barton (1918-1998), and J. W. Comforth and V. Prelog (1906-1998).175 G. J. W. Bremer s experiments, which gave the initial experimental support to van t Hoff s stereochemical views, have been re-assessed through an analysis of the correspondence between the two chemists.176 There is a paper arguing that, in effect, van t Hoff and Le Bel produced two different theories177 and another one suggesting that John Dalton (1766-1844) was the first stereochemist.178 There is a brief analysis of the independent contributions of Alfred Werner and William Jackson Pope (1870-1939) to stereochemistry.179... 

Isatin reacts with ammonium hydroxide or ammonium acetate to furnish a mixture of compounds. Amongst them are isamic acid and its corresponding amide, isamide. Since 1877 there had been a discussion as to their structure, which in 1976 was finally elucidated, by Sir John Comforth on the basis of chemical and spectroscopic data228. Isamic acid can be regarded as a dimer formed by the addition/condensation of one equivalent of ammonia with two equivalents of isatin. This intermediate suffers lactonization and subsequent conversion to isamic acid by an internal nucleophilic attack, where upon the acid is converted to isamide by reaction with a second equivalent of ammonia. 1-Methylisatin reacts similarly, furnishing N-methylisamic acid (Scheme 51). 

On the other hand, the reaction of this chloride with anilines always led to isatin-3-imines. In an attempt to rationalize these contradictory results, it was proposed that 2-chloro-3H-indol-3-one was the substrate but that this compound, which reacts with nucleophiles at the C-2 position, readily hydrolyzed in solvents containing water, thus yielding isatin and products resulting from attack at C-3. Sir John Comforth revisited the chemistry of this... 

For studies on the stereochemistry of enzyme-catalyzed reactions. Sir John Comforth received the Nobel Prize in chemistry in 1975 (sharing it with Vladimir Prelog, page 188). Bom in Australia in 1917, he studied at the University of Sydney and received a Ph.D. from Oxford. His major research was carried out in laboratories at Britain s Medical Research Council and in laboratories at Shell Research Ltd. He was knighted in 1977. 

John Warcup Comforth and Vladimir Prelog for work on the stereochemistry of enz5mie-catalyzed reactions and research into the stereochemistry of organic molecules and reactions. 

In attempting to crystallize crude penicillamine hydrochloride from hot acetone I found that it reacted with the solvent to yield a crystalline thiazolidine. It was thus a p-thiol-a-amino acid. In the Dyson Perrins Laboratory John Comforth deduced from low Kuhn-Roth C—Me values that it contained a gem-dimethyl group and proved by synthesis in October 1943 that it was p-thiol-D-valine. 

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