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Date of Award

4-1981

Degree Type

Thesis

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

Supervisor

J. Warkentin

Abstract

α-Phenylazodimethylcarbinol, a new compound in the series of α-azocarbinols prepared in our laboratory, was synthesized by air oxidation of acetone phenylhydrazone to give the hydroperoxide which is subsequently reduced to the α-azocarbinol by the action of triphenylphosphine. The kinetics of thermolysis of this new compound, along with those of α-phenylazodiphenylcarbinol, α-azoethers, and α-azoacetates, were studied under several reaction conditions in an attempt to further elucidate the decomposition mechanism of these new azo compounds.

Radical intermediates are involved in the chemistry of these α-azocarbinols. The evidence presented reinforces the claim that α-azocarbinols decompose by an induced radical chain mechanism. Such a radical chain process permits the application of these α-azocarbinols, which generate a variety of radicals R (R is phenyl in this research), to the hydroalkylation (hydrophenylation) of several unsaturated compounds.

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