Experiments in the 4-Phenyl-2-cycloalkenone Series. Part I. Synthesis of 2, 9-Diketo-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene

ED Bergmann, J Szmuszkovicz

Index: Bergmann; Szmuszkovicz Journal of the American Chemical Society, 1953 , vol. 75, p. 3226,3229

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Citation Number: 10

Abstract

The methyl ester of the corresponding acid is cyclized by means of sodium alkoxide to 4- phenylcyclohexane-1, 3-dione (11). It was hoped that the carbonyl group in the 1-position would be more prone to form an enol ether III4l5 which could be converted into the desired 4- phenylcyclohex-2-enone (V) by means of treatment with lithium aluminum hydride and subsequent acid hydrolysis. However, the oily enol ethyl ether which was formed when I1 ...