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Issue 24, 2001
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Polyhalogenated BEDT-TTF through chlorination (SO2Cl2, Cl2) and fluorination (®Selectfluor, XeF2) of 5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-one

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Abstract

The electrophilic halogenation of the ethylenic bridge in the 5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-one (1) with SO2Cl2, ®Selectfluor [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)] or XeF2 affords the corresponding monochloro, 1,2-dichloro and monofluoro derivatives 2, 3 and 6, respectively. Reaction with Cl2 gives rise to a pentachloro derivative (5) with syn-Cl2 addition across the unsaturated double bond of 1 characterised by single crystal X-ray diffraction. Homocoupling of 2, 3 or 6 in P(OMe)3 affords the corresponding dichloro, tetrachloro and difluoro BEDT-TTFs 8, 9 and 10, respectively, whose electrochemical characteristics show the electron-withdrawing nature of the halogen substituents present on the ethylenic bridge. Electrocrystallisation of 9 in the presence of (n-Bu4N)2(Mo6Cl14) affords a mixed-valence salt formulated as [9]3[Mo6Cl14], whose X-ray crystal structure has been determined and analysed.

Graphical abstract: Polyhalogenated BEDT-TTF through chlorination (SO2Cl2, Cl2) and fluorination (®Selectfluor, XeF2) of 5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-one

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Publication details

The article was received on 11 Jul 2001, accepted on 23 Oct 2001 and first published on 21 Nov 2001


Article type: Paper
DOI: 10.1039/B106144P
Citation: J. Chem. Soc., Perkin Trans. 1, 2001,0, 3399-3402
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    Polyhalogenated BEDT-TTF through chlorination (SO2Cl2, Cl2) and fluorination (®Selectfluor, XeF2) of 5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-one

    O. J. Dautel and M. Fourmigué, J. Chem. Soc., Perkin Trans. 1, 2001, 0, 3399
    DOI: 10.1039/B106144P

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