New synthetic routes to highly-extended tetrathiafulvalenes

Abstract

Various synthetic routes to highly extended tetrathiafulvalene (TTF) derivatives are presented. They generally involve a (poly)olefination reaction in the last step, thanks to Wittig-type or Horner-Wadsworth-Emmons (HWE) reactions. Two complementary strategies have been carried out by reacting a (poly)formyl-TTF with a phosphorous (P-ylide or phosphonate) reagent, or on the contrary, by the preparation of (poly)phosphonate-TTF derivatives prone to react with aldehydes. An X-ray structural determination of one of these systems confirms the high π-extension of such resulting TTF derivatives.