Chlorosulfination With Thionyl Chloride of Aromatic Methyl Ethers Containing Other Functional Groups

Abstract

Further studies on the direct chlorosulfination with thionyl chloride of aromatic methyl ethers are described. In some cases (e.g. 1,6-dimethoxynaphthalene, 1,2,4 trimethoxybenzene, ethyl 3,5- and 3,7-dimethoxy-2-naphthoate, 3,5-dimethoxyphenyl benzoate) good yields of the sulfinyl chlorides were obtained but in others (e.g. 1,2-dimethoxybenzene, 3,5-dimethoxybenzyl acetate) the products (e.g. thiosulfonates, sulfides) were those from further reactions of the initial sulfinyl chloride. Aromatic methyl ethers containing functional groups which normally undergo reaction with thionyl chloride (e.g. aldehydes, ketones, acetals) showed only the usual reactions of those functional groups and no aromatic chlorosulfination.