SELECTIVE CLEAVAGE OF THE CARBON-SULPHUR AND CARBON-OXYGEN BONDS IN METHOXYTHIOANISOLES

Article abstract of DOI:10.1016/0040-4020(82)80028-8

Selective cleavage of thioether or ether functions in methoxythioanisoles in hexamehtylphosphoramide (HMPA) with sodium gives methoxythiophenols by cleavage of the carbon-sulphur bond.Reactions with sodium isopropanethiolate give instead the thiomethoxyphenols by dealkylation of the methoxy function.When the methoxythioanisoles were treated first with sodium isopropanethiolate and then with sodium complete dealkylation was achieved with formation of mercaptophenols.The present methods have considerable advantages over existing procedures for the synthesis of methoxythiophenols, thiomethoxyphenols and mercaptophenols.The mechanistic implications of the reactions investigated are also discussed.