Synthesis of Some Substituted Adamantane-2,4-diones from 4, 4-disubstituted Cyclohexanone Enamines and Methacryloyl Chloride

Abstract

The reaction of methacryloyl chloride with the morpholine enamine 4a derived from 4-acetyl-4-isopropenylcyclo-hexanone 3a gave 4,6-anti-6-hydroxy-5,6-dimethyl-7-isopropenyladamantane-2,4-dione 6a and 4,6-syn-6-hydroxy-5,6-dimethyl-7-isopropenyladamantane-2, 4-dione 7a as racemates epimeric at 6-C. Comparable results were found for the corresponding phenyl and benzyl substituted cyclohexanones 3b and 3c. In the case of the methyl-substituted cyclohexanone 3d 4,6- anti-alcohol 7d was isolated in pure form.