33314-00-0Relevant academic research and scientific papers
Selective ortho-Methylthiomethylation of Phenols with Dimethyl Sulphoxide and Thionyl Chloride
Sato, Kikumasa,Inoue, Seiichi,Ozawa, Kimio,Tazaki, Michiko
, p. 2715 - 2719 (2007/10/02)
Thionyl chloride and phenyl chlorosulphinate have been shown to be useful activators for dimethyl sulphoxide in the selective preparation of ortho-methylthiomethylphenol via a sigmatropic rearrangement.By this process, ortho-methylthiomethylated phenols having a variety of 2- or 4-substituents (Me, Cl, OMe, NO2, and CO2Me) have been prepared in good yields.In contrast, similar reactions of 3-substituted phenols were affected by the electronic characters of the substituents.With more electron-donating groups such as OH and OMe in the 3-position, none of the expected products were obtained, but in the case of other 3-substituted phenols, two possible rearrangement products were obtained in moderate yields.
