Synthesis 2010(6): 947-952  
DOI: 10.1055/s-0029-1218625
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Divinylsulfides

Jan Paradies*Department of Organic Chemistry, University of Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6088581; e-Mail: jan.paradies@ioc.uka.de;
Further Information

Publication History

Received 19 October 2009
Publication Date:
04 January 2010 (eFirst)

Abstract

Arylacetylenes react with sodium sulfide in the presence of water to yield divinylsulfides. The reaction proceeds in good to excellent yield for both electron-neutral and electron-deficient aromatic systems; for electron-rich aryls, longer reaction times are necessary. The sulfides represent useful substrates for further transformations, for example, oxidation to the corresponding divinylsulfoxides and divinylsulfones. Three selected divinylsulfide derivatives were oxidized selectively to the corresponding sulfoxides or sulfones.