New substrates for the preparation of electroactive materials: the syntheses of chiral tetrathiafulvalene derivatives with hydroxy-functionalised butane-1,4-dithio bridges

Horley, G.A. and Ozturk, T. and Turksoy, F. and Wallis, J.D. (1998) New substrates for the preparation of electroactive materials: the syntheses of chiral tetrathiafulvalene derivatives with hydroxy-functionalised butane-1,4-dithio bridges. Journal of the Chemical Society-Perkin Transactions 1 (19). pp. 3225-3231. ISSN 0300-922X. (The full text of this publication is not available from this repository)

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Official URL
http://dx.doi.org/10.1039/a804779k

Abstract

The syntheses of two derivatives of TTF containing (2R,3R)-2,3-dihydroxybutane-1,4-dithio bridges is described, for use in the preparation of chiral hydrogen bonded radical cation salts as potentially electroactive materials. The bridges are introduced by reaction of 2-thioxo-1,3-dithiole-4,5-dithiolate with 1,4-disubstituted derivatives of bis-O-protected butane-2,3-diol to give a bicyclic thione. The X-ray crystal structure of the isopropylidene ketal derivative shows that all four sp(3) carbon atoms in the eight-membered ring are displaced to the same side of the dithiole plane. Ease of deprotection led to the use of methoxyethoxymethyl (MEM) protecting groups rather than the ketal. Treatment of the bis-MEM-protected bicyclic thione with mercuric acetate and acetic acid led not only to exchange of the exocyclic sulfur for oxygen but also to removal of just one of the MEM groups, which may have wider synthetic applications.

Item Type: Article
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > School of Physical Sciences
Depositing User: R.F. Xu
Date Deposited: 09 Jul 2009 10:00
Last Modified: 09 Jul 2009 10:00
Resource URI: http://kar.kent.ac.uk/id/eprint/17819 (The current URI for this page, for reference purposes)
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