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Russian Chemical Bulletin

, Volume 48, Issue 11, pp 2091–2099 | Cite as

Electrochemical transformations of monooxa- and dioxabicycloalkenes and-bicycloalkanes

  • Yu. N. Ogibin
  • A. O. Terent'ev
  • A. I. Ilovaisky
  • G. I. Nikishin
Organic Chemistry

Abstract

Electrolysis of 2-oxa- and 2,5-dioxabicyclo[n.4.0]alk-1(6)0enes (n=4, 10) under conditions of direct undivided anodic oxidation in methanol results in their electrochemical mono-and dimethoxylation; electrolysis of the corresponding 2-oxa-and 2,5-dioxabicycloalkanes involves electrochemical cleavage of the bridging carbon—carbon bonds followed by electrooxidative transformation into methyl ω-(2-methoxytetrahydrofuryl)-, ω-(dimethoxy-methyl)-, and ω-(1,3-dioxolan-2-yl)alkanoates.

Key words

2-oxa-and 2,5-dioxabicyclo[n.4.0]alkenes and alkanes (n=4, 10) electrochemical cleavage of bridging carbon—carbon bonds ω-substituted methyl alkanoates 

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Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • Yu. N. Ogibin
    • 1
  • A. O. Terent'ev
    • 1
  • A. I. Ilovaisky
    • 1
  • G. I. Nikishin
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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