4526-40-3Relevant 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.
Reaction of Phenols with t-Butyl Bromide-Dimethyl Sulphoxide. Methylthiomethylation versus Bromination
Dossena, Arnaldo,Marchelli, Rosangela,Casnati, Giuseppe
, p. 1141 - 1144 (2007/10/02)
t-Butyl bromide-activated dimethyl sulphoxide reacts with phenols to give either methylthiomethylation or bromination products.Several equilibria are shown to be simultaneously present in the system; however, by appropriate choice of several parameters (basicity, temperature, and reactant ratio) it is possible to drive the reaction selectively in one direction.A general discussion on the mechanism of these reactions is given.
