Intramolecular transfer of complexed radicals as a possible explanation for long-range substituent effects observed in a hydrogen abstraction reaction

DD Newkirk, GJ Gleicher

Index: Newkirk,D.D.; Gleicher,G.J. Journal of the American Chemical Society, 1974 , vol. 96, p. 3543 - 3548

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Citation Number: 5

Abstract

Abstract: A series of 4-methyl-l-phenyl-4-(4-substituted pheny1) pentanes were reacted photolytically with bromotrichloromethane at 70'. Hydrogen abstraction occurred only at the benzylic position. Treatment of the data in a linear free-energy relationship produced ap value of-0.40. This is very large for a system in which the substituted phenyl group is insulated from the reaction site by three saturated carbon atoms. A complementary Taft ...