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

Citation
Yn. Ogibin et al., ELECTROCHEMICAL CLEAVAGE OF A BENZYLIC C-C BOND IN ARYLALIPHATIC COMPOUNDS, Russian chemical bulletin, 42(1), 1993, pp. 126-128
Citations number
20
Categorie Soggetti
Chemistry
Journal title
ISSN journal
10665285
Volume
42
Issue
1
Year of publication
1993
Pages
126 - 128
Database
ISI
SICI code
1066-5285(1993)42:1<126:ECOABC>2.0.ZU;2-S
Abstract
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.