Tetrahedron

Intramolecular nucleophilic attack at silicon in o-silylbenzyl alcohols. Generation of allyl and benzyl anion equivalents

PF Hudrlik, AM Hudrlik, YA Jeilani

Index: Hudrlik, Paul F.; Hudrlik, Anne M.; Jeilani, Yassin A. Tetrahedron, 2011 , vol. 67, # 52 p. 10089 - 10096

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Citation Number: 8

Abstract

Substituted silyl ethers of o-bromobenzyl alcohols and the derived o-silylbenzyl alcohols were used to transfer allyl and benzyl groups from silicon to the electrophiles benzaldehyde and benzophenone in excellent yields. γ-Oxidosilane intermediates (and possibly hypercoordinated silicon intermediates) are postulated.