Regioselective Synthesis of Secondary Allyl Chlorides

Abstract

We have developed high-yielding regiospecific conversions of internal secondary allylic alcohols into rearranged or unrearranged allylic chlorides using thionyl chloride in ether at -70ºC or hexachloroacetone /triphenylphosphine at - 70ºC respectively. The mechanisms of the reactions are discussed.