Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

Vilela, F., Skabara, P. J. , Mason, C. R., Westgate, T. D.J., Luquin, A., Coles, S. J. and Hursthouse, M. B. (2010) Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives. Beilstein Journal of Organic Chemistry, 6, pp. 1002-1014. (doi: 10.3762/bjoc.6.113) (PMID:21085502) (PMCID:PMC2981815)

Abstract

We present a series of compounds by exploiting the unusual 1,4-aryl shift observed for electron-rich 1,3-dithiole-2-thione and tetrathiafulvalene (TTF) derivatives in the presence of perchloric acid. The mechanistic features of this rearrangement are discussed since this synthetic strategy provides an alternative route for the synthesis and functionalisation of sulfur rich compounds including redox active compounds of TTFs, and a Ni dithiolene.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Skabara, Professor Peter
• Authors: Vilela, F., Skabara, P. J., Mason, C. R., Westgate, T. D.J., Luquin, A., Coles, S. J., and Hursthouse, M. B.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Beilstein Journal of Organic Chemistry
• Publisher: Beilstein-Institut
• ISSN: 1860-5397
• ISSN (Online): 1860-5397
• Copyright Holders: Copyright © 2010 Vilela et al
• First Published: First published in Beilstein Journal of Organic Chemistry 6:1002-1014
• Publisher Policy: Reproduced under a Creative Commons license