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.