Synthesis of a Chiral Monosubstituted Derivative of Bis(ethy1enedithio)tetrathiafulvafene: Reaction of the Cyclic Sulfate Ester of R,R-I ,4-Difluorobutane-2,3-diol with 2-Thioxo-l,3-dithiole-4,5-dithiolate

Turan Ozturk, Craig R. Rice, John D. Wallis

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22 Citations (Scopus)

Abstract

2-Thioxo-1,3-dithiole-4,5-dithiolate reacts stereospecifically with the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol by two nucleophilic attacks, ring opening of the cyclic sulfate ester at carbon and displacement of the nearer fluorine atom, to form a derivative of the 1,3-dithiolo[4,5-b]-1,4-dithiin ring system. This product is converted in two steps into an analogue of bis(ethylenedithio)tetrathiafulvalene with a 2-fluoro-1-hydroxyethyl side-chain, a new substrate for the preparation of electroactive materials.

LanguageEnglish
Pages1553-1556
Number of pages4
JournalJournal of Materials Chemistry
Volume5
Issue number10
DOIs
Publication statusPublished - 1995
Externally publishedYes

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Sulfates
Esters
Derivatives
Fluorine
Carbon
Atoms
Substrates
BEDT-TTF

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title = "Synthesis of a Chiral Monosubstituted Derivative of Bis(ethy1enedithio)tetrathiafulvafene: Reaction of the Cyclic Sulfate Ester of R,R-I ,4-Difluorobutane-2,3-diol with 2-Thioxo-l,3-dithiole-4,5-dithiolate",
abstract = "2-Thioxo-1,3-dithiole-4,5-dithiolate reacts stereospecifically with the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol by two nucleophilic attacks, ring opening of the cyclic sulfate ester at carbon and displacement of the nearer fluorine atom, to form a derivative of the 1,3-dithiolo[4,5-b]-1,4-dithiin ring system. This product is converted in two steps into an analogue of bis(ethylenedithio)tetrathiafulvalene with a 2-fluoro-1-hydroxyethyl side-chain, a new substrate for the preparation of electroactive materials.",
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T1 - Synthesis of a Chiral Monosubstituted Derivative of Bis(ethy1enedithio)tetrathiafulvafene

T2 - Journal of Materials Chemistry

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AU - Rice, Craig R.

AU - Wallis, John D.

PY - 1995

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AB - 2-Thioxo-1,3-dithiole-4,5-dithiolate reacts stereospecifically with the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol by two nucleophilic attacks, ring opening of the cyclic sulfate ester at carbon and displacement of the nearer fluorine atom, to form a derivative of the 1,3-dithiolo[4,5-b]-1,4-dithiin ring system. This product is converted in two steps into an analogue of bis(ethylenedithio)tetrathiafulvalene with a 2-fluoro-1-hydroxyethyl side-chain, a new substrate for the preparation of electroactive materials.

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