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

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Author(s): Filipe Vilela | Peter J. Skabara | Christopher R. Mason | Thomas D. J. Westgate | Asun Luquin | Simon J. Coles | Michael B. Hursthouse

Journal: Beilstein Journal of Organic Chemistry
ISSN 1860-5397

Volume: 6;
Issue: 1;
Start page: 1002;
Date: 2010;
Original page

Keywords: aldehydes | metal-coordination | rearrangement | sulfur heterocycles | tetrathiafulvalene

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.

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