Russian Chemical Bulletin

, Volume 42, Issue 1, pp 126–128 | Cite as

Electrochemical cleavage of a benzylic C-C bond in arylaliphatic compounds

  • Yu. N. Ogibin
  • A. I. Ilovaiskii
  • G. I. Nikishin
Organic Chemistry

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.

Key words

substituted alkylbenzenes and anisoles 1,2-dimethoxyindan electrochemical cleavage of a benzylic C-C bond 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • Yu. N. Ogibin
    • 1
  • A. I. Ilovaiskii
    • 1
  • G. I. Nikishin
    • 1
  1. 1.N.D.Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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