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.
TRIMETHYLCHLOROSILANE-MEDIATED FORMATION OF 2-CHLOROCYCLOHEXYL SULPHIDES BY SULPHOXIDES / Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria. - In: JOURNAL OF CHEMICAL RESEARCH. SYNOPSES. - ISSN 0308-2342. - STAMPA. - /:(1987), pp. 24-24.
TRIMETHYLCHLOROSILANE-MEDIATED FORMATION OF 2-CHLOROCYCLOHEXYL SULPHIDES BY SULPHOXIDES
BELLESIA, Franco;GHELFI, Franco;PAGNONI, Ugo Maria
1987
Abstract
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.
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