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

Filipe Vilela, Peter Skabara, Christopher R. Mason, Thomas D. J. Westgate, Asun Luquin, Simon J. Coles, Michael B. Hursthouse

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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.
Original languageEnglish
Pages (from-to)1002-1014
Number of pages13
JournalBeilstein Journal of Organic Chemistry
Volume6
DOIs
Publication statusPublished - 21 Oct 2010

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Keywords

  • aldehydes
  • tetrathiafulvalene
  • metal-coordination
  • sulfur heterocycles

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