Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

Olivier J. Dautel; Jan Larsen; Marc Fourmigué

doi:10.1039/B001996H

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Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

Olivier J. Dautel,^a Jan Larsen^a and Marc Fourmigué*^a

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* Corresponding authors

^a Sciences Moléculaires aux Interfaces, FRE 2068 CNRS, 2, rue de la Houssinière, Nantes, France.
E-mail: fourmigue@cnrs.imn.fr

Abstract

The SO₂Cl₂ chlorination of 5,6-dihydro-1,3-dithiolo[4,5-b]- [1,4]dithiine-2-one affords the corresponding mono- and trans-di-chloro derivatives which eliminate HCl upon treatment with KF/18-crown-6 or LiBr/HMPA, offering an easy route to the unsaturated vinylenedithiotetrathiafulvalene (VDT-TTF).

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Crystal structure data TXT (21K)

Article information

DOI: https://doi.org/10.1039/B001996H
Article type: Communication
Submitted: 10 Mar 2000
Accepted: 16 May 2000
First published: 08 Jun 2000

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Chem. Commun., 2000, 1117-1118

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Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

O. J. Dautel, J. Larsen and M. Fourmigué, Chem. Commun., 2000, 1117 DOI: 10.1039/B001996H

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Chemical Communications

Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

Abstract

Supplementary files

Article information

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Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

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