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

Vilela, Filipe and Skabara, Peter and Mason, Christopher R. and Westgate, Thomas D. J. and Luquin, Asun and Coles, Simon J. and Hursthouse, Michael 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. ISSN 1860-5397

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    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.