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.
- ttf derivatives
- dimeric tetrathiafulvalenes
Bryce, M. R., Skabara, P. J., Moore, A. J., Batsanov, A. S., Howard, J. A. K., & 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), 17781-17794. https://doi.org/10.1016/S0040-4020(97)10243-5