A simple route to novel functionalized tetrathiafulvalene vinylogues

The synthesis and X-ray structural determination of vinylogous tetrathiafulvalenes (TTFV) bearing functional groups on the central conjugation are reported. An unexpected evolution of the bis hydroxymethyl TTFV leading to a derivative, which acts simultaneously as a diene and a dienophile in a Diels–Alder reaction is also described.

Graphical abstractA novel route to vinylogous tetrathiafulvalenes (TTFV) bearing functional groups (R) on the central conjugation has been developed. An unexpected evolution of the bis(hydroxymethyl) TTFV leading to a derivative, which acts simultaneously as a diene and a dienophile in a Diels–Alder reaction is described.Figure optionsDownload full-size imageDownload as PowerPoint slide