ELECTROHYDRODIMERIZATION OF TRANS-CINNAMALDEHYDE

The electrochemical reduction of trans-cinnamaldehyde in protic medium (MeOH-NaClO4) on a mercury cathode gives four cyclic hydrodimeric pro ducts in 80% yield, through a ''head to tail'' coupling pathway. The d ifferent anomers were identified as c-4-phenyl-t-5-[(E)-styryl]tetrahy drofuran-r-2-ol, t-4-phenyl-t-5-[(E)-styryl]tetrahydrofuran-r-2-ol, -c -4-phenyl-t-5-[(E)-styryl]tetrahydrofuran-r-2-ol and -c-4-phenyl-c-5-[ (E)-styryl]tetrahydrofuran-r-2-ol in a ratio of 38:32:27:3 respectivel y. Ethyl glycoside derivatives and lactones have been obtained from th e electrosynthesized products. (C) 1997 Elsevier Science Ltd.