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Synlett 2010(4): 623-627  
DOI: 10.1055/s-0029-1219160
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Aluminium(salen) and Tetrabutylammonium Bromide Catalysed Synthesis of Cyclic Di- and Trithiocarbonates from Epoxides and Carbon Disulfide

Michael North*, Pedro Villuendas
School of Chemistry and University Research Centre in Catalysis and Intensified Processing, Bedson Building, University of Newcastle, Newcastle upon Tyne, NE1 7RU, UK
Fax: +44(191)2226929; e-Mail: michael.north@ncl.ac.uk;
Further Information

Publication History

Received 6 November 2009
Publication Date:
22 December 2009 (online)

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Abstract

The combination of a bimetallic aluminium(salen) complex and tetrabutylammonium bromide was found to catalyse the synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide. Reactions carried out at 50 ˚C produced 1,3-oxa­thiolane-2-thiones, whilst at 90 ˚C, 1,3-dithiolane-2-thiones were formed.

Key words

carbon disulfide - epoxide - aluminium - salen - dithiocarbonate - trithiocarbonate

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