Unexpected Steric Effects of “Remote” Alkyl Groups on the Rate of Conjugate Additions to Alkyl α, β-Ethylenic Sulfones, Sulfoxides, and Esters

AR Usera, GH Posner

Index: Usera, Aimee R.; Posner, Gary H. Journal of Organic Chemistry, 2007 , vol. 72, # 7 p. 2329 - 2334

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Citation Number: 12

Abstract

Examination of conjugated ethylenic sulfones, sulfoxides, and esters in Michael-type addition reactions reveals, for the first time, that the size of the heteroatom-attached alkyl group affects the rate of conjugate addition. Molecular modeling strongly suggests that what are generally considered to be “remote” alkyl groups in-CβH CαHS (O) n alkyl systems and- CH2CβH CαHCOO alkyl systems are actually not remote from the β-carbon atom of the ...