Chemistry–A European Journal

New Reactions of γ??Halocarbanions: Simple Synthesis of Substituted Tetrahydrofurans

M Ma̧kosza, M Judka

Index: Makosza, Mieczyslaw; Judka, Marek Chemistry - A European Journal, 2002 , vol. 8, # 18 p. 4234 - 4240

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Citation Number: 18

Abstract

Abstract The treatment of 4-chlorobutyronitrile, 3-chloropropyl phenyl sulfone, and other related compounds with a base afforded γ-halocarbanions that undergo fast intramolecular substitution of the halogen to produce substituted cyclopropanes. We found that these short- lived carbanionic intermediates can be trapped with active external electrophilic partners, such as aldehydes, to give the aldol anions. These anions then undergo rapid ...