Acid-catalyzed polycondensation of 2-hydroxymethylthiophene and some of its homologues

2-Hydroxymethylthiophene and its acetate were placed in acidic organic medi a of various natures and strengths and at different temperatures. Polyconde nsations involving the alcohol or acetate function and a thiophene proton o nly occurred if the solutions were heated and the acid concentration was re latively high. The thorough assessment of the structure of the ensuing poly mers, including those arising from differently methylated derivatives of th e parent structures, indicated that the electrophilic substitutions had tak en place at all free thiophene sites and that conjugated sequences had also formed. The kinetic and mechanistic features of these systems are examined and discussed in comparison with those displayed by furfuryl alcohol.