Russian Journal of Organic Chemistry

, Volume 49, Issue 6, pp 853–859 | Cite as

Structure of long-lived alkynyl-substituted carbocations of the phenanthrene series and their precursors

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

Abstract

According to the NMR data, 9-(R-ethynyl)-9-hydroxy-10,10-dimethyl-9,10-dihydrophenanthrenes (R = H, Me, Ph) in superacid medium (HSO3F-SO2ClF) at low temperature undergo dehydroxylation with formation of the corresponding long-lived 10,10-dimethyl-9-(R-ethynyl)-9,10-dihydrophenanthren-9-yl cations which do not isomerize to 10-(R-ethynyl)-9,10-dimethyl-9,10-dihydrophenanthren-9-ylium. In contrast, longlived 10,10-dimethyl-9-(3,3,3-trifluoroprop-1-yn-1-yl)-9,10-dihydrophenanthren-9-yl cation derived from 9-(3,3,3-trifluoroprop-1-yn-1-yl)-10,10-dimethyl-9,10-dihydrophenanthren-9-ol undergoes partial isomerization to 10-(3,3,3-trifluoroprop-1-yn-1-yl)-9,10-dimethyl-9,10-dihydrophenanthren-9-yl cation.

Keywords

Oily Substance Ethynyl Ethenyl Conformational Exchange Ethynyl Group 

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Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

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

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