Addition of arylchlorocarbenes to. alpha.,. beta.-unsaturated esters. Absolute rates, substituent effects, and variable reactivities

N Soundararajan, MS Platz, JE Jackson…

Index: Soundararajan, N.; Platz, Matthew S.; Jackson, James E.; Doyle, Michael P.; Oon, Su-Min; et al. Journal of the American Chemical Society, 1988 , vol. 110, # 21 p. 7143 - 7152

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Citation Number: 55

Abstract

Abstract: Addition of arylchlorocarbenes to a, p-unsaturated esters occurs with remarkable facility, even though these carbenes are characterized as electrophilic. Reactions with diethyl maleate, which exhibits isomerization to diethyl fumarate and produces cyclopropanes formally derived from both olefin geometries, are most simply interpreted as concerted additions with isomerization of diethyl maleate resulting from a chemical ...