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 › peer-review

8 Citations (Scopus)

207 Downloads (Pure)

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 language	English
Pages (from-to)	1002-1014
Number of pages	13
Journal	Beilstein Journal of Organic Chemistry
Volume	6
DOIs	https://doi.org/10.3762/bjoc.6.113
Publication status	Published - 21 Oct 2010

Keywords

aldehydes
tetrathiafulvalene
metal-coordination
sulfur heterocycles

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10.3762/bjoc.6.113

Skabara_BJOC_-_Rearrangement_revised.docAccepted author manuscript, 5.67 MB

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2 Finished

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)
Murphy, J., Coombs, G., Ferguson, A. & Florence, A.
Scottish Funding Council SFC, EPSRC (Engineering and Physical Sciences Research Council)
1/09/07 → 30/10/12
Project: Research
SELF ASSEMBLING CONJUGATED MACROMOLECULES FOR ORGANIC FIELD EFFECT TRANSISTORS AND SOLAR CELLS
Skabara, P.
EPSRC (Engineering and Physical Sciences Research Council)
1/04/07 → 31/05/10
Project: Research

Cite this

@article{bd2175beea4b409b909299a85a140056,

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

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.}",

year = "2010",

month = oct,

day = "21",

doi = "10.3762/bjoc.6.113",

language = "English",

volume = "6",

pages = "1002--1014",

journal = "Beilstein Journal of Organic Chemistry ",

issn = "1860-5397",

}

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 › peer-review

TY - JOUR

T1 - Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

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.

PY - 2010/10/21

Y1 - 2010/10/21

N2 - 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.

AB - 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.

KW - aldehydes

KW - tetrathiafulvalene

KW - metal-coordination

KW - sulfur heterocycles

UR - http://www.scopus.com/inward/record.url?scp=78751490494&partnerID=8YFLogxK

U2 - 10.3762/bjoc.6.113

DO - 10.3762/bjoc.6.113

M3 - Article

VL - 6

SP - 1002

EP - 1014

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

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

Abstract

Keywords

Access to Document

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

SELF ASSEMBLING CONJUGATED MACROMOLECULES FOR ORGANIC FIELD EFFECT TRANSISTORS AND SOLAR CELLS

Cite this