TRIMETHYLCHLOROSILANE-MEDIATED FORMATION OF 2-CHLOROCYCLOHEXYL SULPHIDES BY SULPHOXIDES

The title 2-chlorocyclohexyl sulfides, e.g. I (R = Me, Et, Me2CH, Bu) were prepd. by treating cyclohexene with the corresponding alkyl sulfoxides RSOR in the presence of Me3SiCl. Unsym. sulfoxides, e.g. EtSOBu gave a mixt. of products I (R = Et, Bu). Tetramethylene sulfoxide (II) gave aldehyde I (R = CH2CH2CH2CHO) as the major product. A mechanism is presented in which 2 mol. of sulfoxide form an intermediates S-alkoxysulfonium salt.