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Paper | Regular issue | Vol 48, No. 10, 1998, pp.2003-2017
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8230
Free Radical Reaction of Diisopropyl Xanthogen Disulfide with Unsaturated Systems

Yves Gareau* and André Beauchemin

*Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe-Claire-Dorval, Quebec, H9R 4P8, Canada

Abstract

1,3-Dithiol-2-ones are prepared in one pot reaction from commercially available diisopropyl xanthogen disulfide (2) and alkynes under radical conditions. The 5-membered heterocycle is formed via a ring closure of vinyl radical (7) resulting from the thio radical addition of 5 to an alkyne. The reaction worked best for alkynes conjugated with a C=C double bond. The oxygen atoms of reagent (2) could be replaced by sulfur and this new reagent furnished 1,3-dithiol-2-thiones under radical conditions.