Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives
Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives
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.
aldehydes, metal-coordination, rearrangement, sulfur heterocycles, tetrathiafulvalene
1002-1014
Vilela, Filipe
196d0a91-a43f-490b-9d80-8f1a627f1d99
Skabara, Peter J.
7138e414-7d50-41c7-933e-0bccad2fa4cd
Mason, Christopher R.
2a4ed3f3-c0bb-41e0-b71a-6282285a5d1b
Westgate, Thomas D.J.
d506b51e-422d-493c-9743-e0b626c64944
Luquin, Asun
1043e70c-e1b9-47d6-be38-ee0a6b21232f
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
21 October 2010
Vilela, Filipe
196d0a91-a43f-490b-9d80-8f1a627f1d99
Skabara, Peter J.
7138e414-7d50-41c7-933e-0bccad2fa4cd
Mason, Christopher R.
2a4ed3f3-c0bb-41e0-b71a-6282285a5d1b
Westgate, Thomas D.J.
d506b51e-422d-493c-9743-e0b626c64944
Luquin, Asun
1043e70c-e1b9-47d6-be38-ee0a6b21232f
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Vilela, Filipe, Skabara, Peter J., Mason, Christopher R., Westgate, Thomas D.J., Luquin, Asun, 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, .
(doi:10.3762/bjoc.6.113).
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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Published date: 21 October 2010
Keywords:
aldehydes, metal-coordination, rearrangement, sulfur heterocycles, tetrathiafulvalene
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 346197
URI: http://eprints.soton.ac.uk/id/eprint/346197
ISSN: 1860-5397
PURE UUID: d8125947-ad38-4d92-85ae-c4051b01c205
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Date deposited: 17 Dec 2012 10:20
Last modified: 15 Mar 2024 03:01
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Contributors
Author:
Filipe Vilela
Author:
Peter J. Skabara
Author:
Christopher R. Mason
Author:
Thomas D.J. Westgate
Author:
Asun Luquin
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