Issue 0, 1979

Enamine chemistry. Part 26. Preparation of substituted adamantane-2,4-diones and bicyclo[2.2.2]octan-2-ones

Abstract

Reaction of αβ-unsaturated acid chlorides with the morpholine or pyrrolidine enamines derived from 4-benzoyl-4-methylcyclohexanone gives the corresponding 6-hydroxy-7-methyl-6-phenyladamantane-2, 4-dione in moderate to good yield. Enamines from 4-acetyl-4-phenyl (or 4-ethoxycarbonyl) cyclohexanone could not be isolated owing to their preferential cyclisation into 1 -phenyl (or 1 -ethoxycarbonyl) 4-substituted aminobicyclo[2.2.2]octan-2-ones.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 2180-2183

Enamine chemistry. Part 26. Preparation of substituted adamantane-2,4-diones and bicyclo[2.2.2]octan-2-ones

S. A. Ahmed and P. W. Hickmott, J. Chem. Soc., Perkin Trans. 1, 1979, 2180 DOI: 10.1039/P19790002180

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