Synlett 2002(11): 1762-1778
DOI: 10.1055/s-2002-34863
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Chemistry of Tetrathiomolybdate: Applications in Organic Synthesis

Kandikere Ramaiah Prabhu, Naduthambi Devan, Srinivasan Chandrasekaran*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India
Fax: +91(80)3600529; e-Mail: scn@orgchem.iisc.ernet.in;
Further Information

Publication History

Received 24 October 2001
Publication Date:
21 October 2002 (online)

Abstract

The utility of tetrathiomolybdate in a variety of organic transformations is presented in this account. The sulfur transfer ability of tetrathiomolybdate is exploited in the synthesis of organic disulfides under mild reaction conditions. The induced internal redox reactions associated with tetrathiomolybdate have been thoroughly exploited in developing various methodologies, which include the reduction of organic azides, synthesis of diselenides, cyclic imines, thioamides, and thiolactams. In addition, novel deprotection strategies using tetrathiomolybdate have been developed to cleave the propargyl and propargyloxy carbonyl (POC) protecting groups. Tetrathiomolybdate mediated tandem sulfur transfer-reduction-Michael reactions have been applied to the synthesis of sulfur containing bicyclic systems. Furthermore, the reactions in the solid state and the reactions in water medium assisted by tetrathiomolybdate have greatly simplified the synthesis of organic disulfides.

1

Honorary Professor, Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore.

11

Available commercially from the Aldrich Chemical Co. USA.

85

Unpublished results Sinha, S.; Chandrasekaran, S.

99

Bhar, D.; Chandrasekaran, S. Unpublished results.