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Synthesis of new mono-functionalised tetrathiafulvalene derivatives by reactions of tetrathiafulvalenyllithium with aldehydes and ketones: X-ray crystal structures of TTF-CMe(OH)Fc, TTF-CMe(OMe)Fc and TTF-CH(OMe)TTF (Fc = ferrocenyl)

Bryce, M.R. and Skabara, P.J. and Moore, A.J. and Batsanov, A.S. and Howard, J.A.K. and Hoy, V.J. (1997) Synthesis of new mono-functionalised tetrathiafulvalene derivatives by reactions of tetrathiafulvalenyllithium with aldehydes and ketones: X-ray crystal structures of TTF-CMe(OH)Fc, TTF-CMe(OMe)Fc and TTF-CH(OMe)TTF (Fc = ferrocenyl). Tetrahedron, 53 (52). pp. 17781-17794. ISSN 0040-4020

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Abstract

Reactions of tetrathiafulvalenyllithium (TTF-Li) with a range of aldehydes and ketones have been explored for the first time, to provide an efficient route to mono-functionalised TTF derivatives of general formulae TTF-CH(OH)R (R = alkyl, phenyl, tetrathiafulvalenyl and ferrocenyl) and TTF-CR(OH)R' (R = alkyl, phenyl R' = alkyl, phenyl, tetrathiafulvalenyl, ferrocenyl and R-R' = fluorenyl). Subsequent transformations involving the reactive alcohol group of some of these compounds are reported. The structures of the three title compounds have been established by single-crystal X-ray analysis.