Abstract

Abstract The Michael addition of diethyl malonate to ethyl crotonate-(carbonyl-C14) was carried out with one equivalent of sodium ethoxide. The addition product, diethyl α-ethoxycarbonyl-β-methylglutarate, was hydrolyzed to the corresponding acid. It was decarboxylated by heating to give β-methylglutaric acid, which was found to contain most of the radioactivity originally present in the ethyl crotonate. Thus, it was demonstrated that the migration of an ethoxycarbonyl group did not take place in contrast to the case with diethyl methylmalonate. The mechanism is discussed.

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