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

Article abstract of DOI:10.1021/jo00098a039

Triphenylphosphine and tetrachloromethane react cleanly in refluxing tetrahydrofuran with substituted γ- and δ-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 of protecting groups.Application of this methodology to the dichloroolefination of simple lactones, suger-derived lactones, and other biologically significant lactones is described.