Russian Chemical Bulletin

, Volume 42, Issue 1, pp 118–123 | Cite as

The formation of tetracyclo[7.2.1.02,5.02,8]dodeca-6,10-dienes under conditions of thermal isomerization of spiro[2.4]hepta-4,6-diene into bicyclo[3.2.0]hepta-1,3-diene

  • Yu. V. Tomilov
  • A. B. Kostitsyn
  • E. V. Shulishov
  • O. M. Nefedov
Organic Chemistry
  • 35 Downloads

Abstract

The formation of the novel hydrocarbons, tetracyclo[7.2.1.02,5.02,8]dodecadienes, as a result of thermal isomerization of spiro[2.4]hepta-4,6-diene into bicyclo[3.2.0]hepta-1,3-diene and its capture by 1,3-dienes is demonstrated. The conditions of thermal isomerization and dimerization of the spiroheptadiene are studied. Cyclopropanation of the polycyclic dienes formed by diazomethane in the presence of Pd-catalysts was accomplished, and occured solely through the norbornene double bond.

Key words

spiro[2.4]hepta-4,6-diene bicyclo[3.2.0]hepta-1,3-diene tetracyclo[7.2.1.02,5.02,8]dodeca-6,10-dienes thermal isomerization of spiroheptadiene Diels-Alder synthesis catalytic cyclopropanation with diazomethane 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • Yu. V. Tomilov
    • 1
  • A. B. Kostitsyn
    • 1
  • E. V. Shulishov
    • 1
  • O. M. Nefedov
    • 1
  1. 1.N.D.Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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