On the Relationship between Strain and Chemical Reactivity of Torsionally Distorted Carbon-Carbon Double Bonds

  • Kenneth J. Shea
Part of the NATO ASI Series book series (ASIC, volume 273)


In an effort to develop relationships between the strain of a carbon-carbon double bond and its chemical reactivity, a series of bridgehead alkenes containing torsionally distorted bridgehead double bonds have been synthesized. A combination of computational, spectroscopic and structural studies have provided information regarding the manner and degree of strain in these molecules. In addition, the rates of expoxidation of these double bonds have been obtained. The relationship between strain energy, reaction exothermicity and other spectroscopic parameters to the rate of epoxidation are examined in an effort to identify the chemical manifestations of strain.


Double Bond Chemical Reactivity Spectroscopic Parameter Torsionally Distort SIGMATROPIC Rearrangement 
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Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • Kenneth J. Shea
    • 1
  1. 1.Department of ChemistryUniversity of CaliforniaIrvineUSA

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