The Journal of Organic Chemistry

Vinyl sulfone bicycloannulation of cyclohexenones: one-step synthesis of tricyclo [3.2. 1.02, 7] octan-6-ones

RM Cory, RM Renneboog

Index: Cory, Robert M.; Renneboog, Richard M. Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 3898 - 3904

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Citation Number: 29

Abstract

Vinyl sulfones bicyclowulate the d-enolatea of a-cyclohexenones in the presence of hexamethylphosphoramide in refluxing tetrahydrofuran to give tricyclo [3.2. 1.02~ 7] octan-6- ones in a single synthetic step. In the case of 8-methylcyclohexenones this method gives higher yields than vinylphosphonium bicycloannulation, but with cu-methylcyclohexenones the opposite is true. The reaction is successful with both aryl vinyl sulfones and aryl ...