The Journal of Organic Chemistry

Dichloromethylenation of Lactones. 6. Efficient Synthesis of Dichloroolefins from Lactones and Acetates Using Triphenylphosphine and Tetrachloromethane

M Lakhrissi, Y Chapleur

Index: Lakhrissi, Mohamed; Chapleur, Yves Journal of Organic Chemistry, 1994 , vol. 59, # 19 p. 5752 - 5757

Full Text: HTML

Citation Number: 58

Abstract

Triphenylphosphine and tetrachloromethane react cleanly in refluxing tetrahydrofuran with substituted y-and &lactones and some esters to afford the corresponding dichloroolefins in good yields. This new Wittig-type reaction provides an easy entry to this new class of compounds and tolerates a large variety of protecting groups. Application of this methodology to the dichloroolefination of simple lactones, sugar-derived lactones, and ...