Reaction of α-Halosulfoxides with Amines

摘要: When optically active bromomethyl p-toly sulfoxide was treated with sodium methylmercaptide or ethoxide, α-substituted methyl sulfoxides were obtained in good yields. By contrast, reaction secondary amines produced achiral p-toluenesulfenamides, methylenediamines, and amine hydrobromides nearly quantitative The an is presumed to proceed through the initial nucleophilic substitution at α-carbon of form aminomethyl sulfoxide, followed by rearrangement corresponding sulfenate, subsequent attack sulfur atom sulfenate final product. Meanwhile, a facile interconversion alkoxymethyl also observed.