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

Filipe Vilela; Peter J 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 J 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 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
metal-coordination
rearrangement
sulfur heterocycles
tetrathiafulvalene
FIELD-EFFECT TRANSISTORS
ELECTRONIC-PROPERTIES
HIGH-MOBILITY
COMPLEXES
ELECTROPOLYMERIZATION
CHEMISTRY
LIGANDS
DONORS
OFETS
TTF

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@article{06fb0a44b10344eaa51b1a7d7216ba68,

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, metal-coordination, rearrangement, sulfur heterocycles, tetrathiafulvalene, FIELD-EFFECT TRANSISTORS, ELECTRONIC-PROPERTIES, HIGH-MOBILITY, COMPLEXES, ELECTROPOLYMERIZATION, CHEMISTRY, LIGANDS, DONORS, OFETS, TTF",

author = "Filipe Vilela and Skabara, {Peter J} 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",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

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 J

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 - metal-coordination

KW - rearrangement

KW - sulfur heterocycles

KW - tetrathiafulvalene

KW - FIELD-EFFECT TRANSISTORS

KW - ELECTRONIC-PROPERTIES

KW - HIGH-MOBILITY

KW - COMPLEXES

KW - ELECTROPOLYMERIZATION

KW - CHEMISTRY

KW - LIGANDS

KW - DONORS

KW - OFETS

KW - TTF

U2 - 10.3762/bjoc.6.113

DO - 10.3762/bjoc.6.113

M3 - Article

SN - 1860-5397

VL - 6

SP - 1002

EP - 1014

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Keywords

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