Russian Journal of Organic Chemistry

, Volume 47, Issue 6, pp 862–868 | Cite as

Behavior of 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium: Opening of the cyclopropane ring

  • A. M. Genaev
  • G. E. Sal’nikov
  • V. G. Shubin


According to the NMR data, opening of the cyclopropane ring in carbocations derived from 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium follows two pathways, depending on the acidity. The first pathway is protonation of the cyclopropyl group; it occurs in strongly acidic medium (HSO3F-SbF5-SO2ClF-CD2Cl2). The second pathway involves cyclopropyl-carbinyl rearrangement; it is typical of less acidic medium.


Cyclopropane Cyclopropyl Cyclopropane Ring Cation Versus Cyclopropyl Group 
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Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • A. M. Genaev
    • 1
  • G. E. Sal’nikov
    • 1
  • V. G. Shubin
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

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