Radical, one-step approach to o-chlorophenyl thioethers from xanthates. a rapid access to vinylsilanes.

[摘要]：Radical substitution of the xanthate group in alkyl xanthates R1CH2CH2CHXR2 [4a-o; X = SC(S)(OEt)] for 2-chlorophenyl thioether proceeds cleanly under stoichiometric dilauroyl peroxide initiation, giving alkyl aryl thioethers R1CH2CH2CH(S-1,2-C6H4Cl)R2 (7a-o; R1 = aralkyl, aroyl, phosphonoacetyl, hetaryl, carbocyclyl, heterocyclyl; R2 = SiMe3, alkyl, OCOtBu, N-Boc-amino, phthalimidomethyl, CH2SiMe3, CH2Ph, etc.). Synthetic potential of the prepd. thioethers was demonstrated by oxidn. to sulfoxides and sulfenic acid elimination, which afforded the corresponding alkenes and vinylsilanes R1CH2CH:CHR2 (13-17). The compd. 13, 3-methyl-3-[(2E)-3-(trimethylsilyl)-2-propen-1-yl]cyclohexanone was converted to the corresponding enyne (E)-O:C6H8-3-Me-3-CH2CH:CHCYCPh (19) by iodination with N-iodosuccinimide and Sonogashira coupling with phenylacetylene.

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