Stereochemistry of decarbalkoxylation of cyclic geminal diesters effected by water and lithium chloride in dimethyl sulfoxide

AP Krapcho, JF Weimaster

Index: Krapcho, A. Paul; Weimaster, John F. Journal of Organic Chemistry, 1980 , vol. 45, # 21 p. 4105 - 4111

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Citation Number: 33

Abstract

The stere'ochemical consequences of the decarbalkoxylation of cyclic geminal diesters by LiCl-H20-Me2S0 have been examined. The norbornene diester 13 and the norbornane diester 16 lead predominantly to the exo esters 14 and 17, respectively. The 2- methylcyclohexane diester 22 leads to esters containing more cis (23) than trans (24) isomer. The diesters 19, 25, and 28 lead to nearly equal amounts of the cis and trans ...