Synthesis 2006(17): 2815-2817  
DOI: 10.1055/s-2006-942520
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Straightforward Access to Mono- and Bis(pyrrolo)tetrathiafulvalenes

Jean-Yves Balandier, Ahmed Belyasmine, Marc Sallé*
Laboratoire de Chimie et Ingénierie Moléculaire des Matériaux d’Angers (CIMMA), Groupe Synthèse Organique et Matériaux Fonctionnels (SOMaF), UMR CNRS 6200, Université d’Angers, 2 Bd Lavoisier, 49045 Angers, France
Fax: +33(2)41735405; e-Mail: marc.salle@univ-angers.fr;
Further Information

Publication History

Received 20 April 2006
Publication Date:
25 July 2006 (online)

Abstract

An alternative efficient synthetic procedure to mono- and bis(pyrrolo)tetrathiafulvalenes is proposed starting from 4,4-diethoxybut-2-ynal.

9

Compound 2 is commercially available from Acros Organics.

11

Attempts to purify imine 4 by silica gel or alumina chromatography invariably led to a partial reverse reaction to the starting products.

12

Alternatively, compound 5 may be directly engaged in the following step without being chromatographed (no noticeable loss in the yield of 6). In fact, the purification of 5 by silica gel chromatography is accompanied by formation of compound 6.

13

We observed lower yields with longer times.