Synthesis of bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) derivatives functionalised with two, four or eight hydroxyl groups

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Brown, R.J., Brooks, A.C., Griffiths, J.P., Vital, B., Day, P. and Wallis, J.D. ORCID: 0000-0001-7259-8783, 2007. Synthesis of bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) derivatives functionalised with two, four or eight hydroxyl groups. Organic & Biomolecular Chemistry, 5 (19), pp. 3172-3182.

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Official URL: http://dx.doi.org/10.1039/B709823E

Abstract

Short synthetic routes to a range of BEDT-TTF derivatives functionalised with two, four or eight hydroxyl groups are reported, of interest because of their potential for introducing hydrogen bonding between donor and anion into their radical cation salts. The cycloaddition of 1,3-dithiole-2,4,5-trithione with alkenes to construct 5,6-dihydro-1,3-dithiolo[4,5-b]1,4-dithiin-2-thiones is a key step, with homo- or hetero-coupling procedures and O-deprotection completing the syntheses. The first synthesis of a single diastereomer of tetrakis(hydroxymethyl)BEDT-TTF, the cis, trans product, was achieved by careful choice of O-protecting groups to facilitate separation of homo- and hetero-coupled products. Cyclisation of the trithione with enantiopure 1R,2R,5R,6R-bis(O,O-isopropylidene)hex-3-ene-1,2,5,6-tetrol (from D-mannitol) gave two separable diastereomeric thiones, which can be transformed to enantiomeric BEDT-TTF derivatives with four or eight hydroxyl groups.

Item Type:

Journal article

Publication Title:

Organic & Biomolecular Chemistry

Creators:

Brown, R.J., Brooks, A.C., Griffiths, J.P., Vital, B., Day, P. and Wallis, J.D.

Publisher:

Royal Society of Chemistry

Place of Publication:

Cambridge

Date:

2007