Russian Chemical Bulletin p. 126 - 128 (1993)
Update date:2022-08-25
Topics:
Ogibin, Yu. N.
Ilovaiskii, A. I.
Nikishin, G. I.
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 most effective for substituted benzenes and anisoles with side chains bearing vicinal methoxy- and hydroxy-groups in the α- and β-positions.Cleavage was moderate for α- or 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.
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