Journal of Organic Chemistry p. 132 - 136 (1982)
Update date:2022-08-05
Topics:
Cristol, Stanley J.
Seapy, Dave G.
O-Alkyl-S-methyl xanthates have been used to convert alcohols to alkyl halides via free-radical pathways.The xanthate esters were readily prepared in high yields and were converted in 8-80percent yields to the corresponding alkyl halides by (a) photolysis with 254-nm light in carbon tetrachloride or bromotrichloromethane and (b) by treatment with Cu(I)-Cu(II) halide in acetonitrile.The photochemical transformation gave low yields with highly aliphathic compounds due to carbon tetrachloride-mediated free-radical halogenation reactions.The transformation promoted by Cu(I)-Cu(II) halide competed with an electron-transfer oxidation process.The reaction could not be induced with AIBN or benzoyl peroxide or by treatment with molybdenum pentachloride.Mechanistic implications are discussed.
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