Russian Chemical Bulletin

, Volume 46, Issue 3, pp 507–510 | Cite as

Synthesis of polycyclic cyclopropanecarboxylic acids and their esters based on catalytic cyclopropanation of 6,6-dimethylfulvene

  • Yu. V. Tomilov
  • N. M. Tsvetkova
  • O. M. Nefedov
Organic Chemistry

Abstract

Reactions of 6,6-dimethylfulvene with methyl diazoacetate in the presence of Cu compounds is accompanied by methoxycarbonylmethylenation of the endocyclic double bonds to give the corresponding mono- and diadducts in total yields of up to 85% with marked predominance ofanti-isomers. The subsequent cyclopropanation of monoadducts with diazomethane in the presence of Pd compounds also involves the endocyclic double bond and gives esters of tricyclo[4.1.0.0.2,4]heptanecarboxylic acid in high yields.

Key words

diazomethane diazoesters cyclopropanation esters of bicyclo[3.1.0]hex-2-ene-6-and tricyclo[4.1.0.02,4]heptane-3-carboxylic acids 

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Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • Yu. V. Tomilov
    • 1
  • N. M. Tsvetkova
    • 1
  • O. M. Nefedov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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