Showing papers by "Yu. N. Ogibin published in 1993"
TL;DR: In this paper, the effect of the structure of alkyl and aryl fragments on the process of a benzylic C-C bond cleavage was studied and the most effective side chains with side chains bearing vicinal methoxy-and hydroxy-groups in the a-and β-positions were found to be substituted benzenes and anisoles, and moderate for β-methoxy(hydroxy)- and (β,β-dialkoxyalkyl)arenes.
Abstract: Electrochemical cleavage of a benzylic C-C bond in arylaliphatic compounds and the effect of the structure of their alkyl and aryl fragments on the process are studied. Cleavage was found to be the most effective for substituted benzenes and anisoles with side chains bearing vicinal methoxy- and hydroxy-groups in the a- and β-positions. Cleavage was moderate for cior β-methoxy(hydroxy)- and (β,β-dialkoxyalkyl)arenes. Electrolysis carried out in methanol results in formation of PhCH2OMe and PhCH(OMe)2 from PhCH2R and PhCH(OMe)R, benzaldehyde from (1,2-dihydroxypropyl)benzene, acetophenone from 2-phenylhexan-2-ol, 4-MeOC6H4CH(OMe)2 from 4-(1,2-dimethoxypropyl)anisole, and 2-(MeO)2CHC6H4CH(OMe)2 from 1,2-dimethoxyindan.
4 citations