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

doi:10.3762/bjoc.6.113

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article

8 Citations (Scopus)

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.

Language	English
Pages	1002-1014
Number of pages	13
Journal	Beilstein Journal of Organic Chemistry
Volume	6
DOIs	10.3762/bjoc.6.113
Publication status	Published - 21 Oct 2010

Fingerprint

Thiones

Sulfur

Derivatives

Electrons

Perchloric Acid

Oxidation-Reduction

tetrathiafulvalene

Keywords

aldehydes
tetrathiafulvalene
metal-coordination
sulfur heterocycles

Cite this

Vilela, F., Skabara, P., Mason, C. R., Westgate, T. D. J., Luquin, A., Coles, S. J., & 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, 1002-1014. https://doi.org/10.3762/bjoc.6.113

Vilela, Filipe ; Skabara, Peter ; Mason, Christopher R. ; Westgate, Thomas D. J. ; Luquin, Asun ; Coles, Simon J. ; Hursthouse, Michael B. / Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives. In: Beilstein Journal of Organic Chemistry. 2010 ; Vol. 6. pp. 1002-1014.

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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.",

keywords = "aldehydes, tetrathiafulvalene , metal-coordination, sulfur heterocycles",

author = "Filipe Vilela and Peter Skabara and Mason, {Christopher R.} and Westgate, {Thomas D. J.} and Asun Luquin and Coles, {Simon J.} and Hursthouse, {Michael B.}",

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Vilela, F, Skabara, P, Mason, CR, Westgate, TDJ, Luquin, A, Coles, SJ & Hursthouse, MB 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, vol. 6, pp. 1002-1014. https://doi.org/10.3762/bjoc.6.113

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives. / Vilela, Filipe; Skabara, Peter; Mason, Christopher R.; Westgate, Thomas D. J.; Luquin, Asun; Coles, Simon J.; Hursthouse, Michael B.

In: Beilstein Journal of Organic Chemistry, Vol. 6, 21.10.2010, p. 1002-1014.

Research output: Contribution to journal › Article

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AU - Vilela, Filipe

AU - Skabara, Peter

AU - Mason, Christopher R.

AU - Westgate, Thomas D. J.

AU - Luquin, Asun

AU - Coles, Simon J.

AU - Hursthouse, Michael B.

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KW - aldehydes

KW - tetrathiafulvalene

KW - metal-coordination

KW - sulfur heterocycles

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