Free radical hydrogen abstraction from benzocycloalkenes Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/r494vn59f

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  • The relative rates of hydrogen abstraction from o-xylene, o-diethylbenzene and a series of four benzocycloalkenes by trichloromethyl radical were determined at 70°. The strain energies of the hydrocarbons and the corresponding radicals were calculated. A good correlation between the log of the relative rates and the calculated changes in strain energy, with a coefficient of -0.974, was obtained. The results showed that in free radical substitutions, benzocycloalkenes are less dependent on strain factors than polycycloalkanes. This is due to the benzylic-type radicals formed in the former series being greatly stabilized by resonance and hence somewhat insensitive to other structural factors.
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