Theoretical and Experimental Chemistry

, Volume 38, Issue 4, pp 229–236 | Cite as

[3.3.2]- and [3.3.3]Propellanes in Reactions with Oxidizing Electrophiles

  • T. E. Shubina
  • P. A. Gunchenko
  • T. S. Vigovskaya
  • P. R. Schreiner
  • A. G. Yurchenko
  • A. A. Fokin
Article

Abstract

The structure of [3.3.2]- and [3.3.3]propellanes, their framework analogs, and their radical-cations was investigated by computational methods (BLYP and B3LYP) in the 6-31G* basis set. The reactivity of the propellanes toward model oxidizing electrophiles does not contradict the quantum-chemical calculations. In the case of the tetracyclic framework analog of [3.3.3]propellane the reaction takes place as C—H substitution, whereas in the case of [3.3.2]propellanes it takes place as C—C-oxidative addition.

propellane radical-cation single-electron transfer quantum-chemical calculation 

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Copyright information

© Plenum Publishing Corporation 2002

Authors and Affiliations

  • T. E. Shubina
    • 1
  • P. A. Gunchenko
    • 1
  • T. S. Vigovskaya
    • 1
  • P. R. Schreiner
    • 2
  • A. G. Yurchenko
    • 1
  • A. A. Fokin
    • 1
  1. 1.National Technical University of Ukraine "Kyiv Polytechnic Institute,"KyivUkraine
  2. 2.Department of ChemistryUniversity of GeorgiaAthensUSA

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