A novel synthesis of functional dithioesters, dithiocarbamates, xanthates and trithiocarbonates

A novel synthesis of functional dithioesters, dithiocarbamates, xanthates and trithiocarbonates is described. Heating a bis(thiocarbonyl) disulfide with an azo-compound results in the formation of (thiocarbonyl)sulfanyl derivatives in moderate to high yield. The process is proposed as the method of...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 12; pp. 2435 - 2438
Main Authors Thang, San H., Chong, (Bill)Y.K., Mayadunne, Roshan T.A., Moad, Graeme, Rizzardo, Ezio
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.03.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet full text

Cover

More Information
Summary:A novel synthesis of functional dithioesters, dithiocarbamates, xanthates and trithiocarbonates is described. Heating a bis(thiocarbonyl) disulfide with an azo-compound results in the formation of (thiocarbonyl)sulfanyl derivatives in moderate to high yield. The process is proposed as the method of choice for preparing tertiary (thiocarbonyl)sulfanyl compounds and is compatible with a wide range of functionalities ( e.g. carboxy, hydroxy and nitrile). The reaction between alkyl radicals and bis(thiocarbonyl) disulfides provides a novel route to functional (thiocarbonyl)sulfanyl derivatives.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00177-X