Electrochemical cleavage of a benzylic C-C bond in arylaliphatic compo
unds and the effect of the structure of their alkyl and aryl fragments
on the process are studied. Cleavage was found to be the most effecti
ve for substituted benzenes and anisoles with side chains bearing vici
nal methoxy- and hydroxy-groups in the alpha- and beta-positions. Clea
vage was moderate for alpha- or beta-methoxy(hydroxy)- and (beta,beta-
dialkoxyalkyl)arenes. Electrolysis carried out in methanol results in
formation of PhCH2OMe and PhCH(OMe)2 from PhCH2R and PhCH(OMe)R, benza
tdehyde from (1,2-dihydroxypropyl)benzene, acetophenone from 2-phenylh
exan-2-ol, 4-MeOC6H4CH(OMe) from 4-(1,2-dimethoxypropyl)anisole, and 2
-(MeO)2CHC6H4CH(OMe)2 from 1,2-dimethoxyindan.