L. Munday
Jun 17, 1961
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Journal
Nature
Abstract
THE reaction of 2- and 4-alkylcyclohexanones in the Strecker and Bucherer hydantoin reactions leads to geometrically isomeric alkylcyclohexane-1-amino-1-carboxylic acids. Paper chromatographic analysis shows that the crude product of the Strecker reaction consists of one isomer only, while the main product from the Bucherer reaction has the alternative configuration. Assuming the configuration of the 4-alkyl derivatives to be indicated by the sluggish hydrolysis of the 1-amino-4-tert-butylcyclohexyl-cyanide hydrochloride1 in the Strecker synthesis, then the Bucherer products must have the opposite configuration.