ELECTROCHEMICAL CLEAVAGE OF A BENZYLIC C-C BOND IN ARYLALIPHATIC COMPOUNDS

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.