Date of Award

6-1976

Document Type

Union College Only

Degree Name

Bachelor of Science

Department

Chemistry

Language

English

Abstract

0-(phenyl)hydroxylamine and its p-nitrated derivative were synthesized for use in a study of substitution reactions at an sp3 hybridized nitrogen atom. The 0-(phenyl)hydroxylamine was decomposed thermally in several nonnucleophilic solvents and in water, with base present. It is proposed that in organic solvents, the decomposition proceeds by a radical mechanism involving a solvent cage intermediate. Ammonia and aminophenols are the major products. In water, it appears that an SN1 reaction producing phenoxide may compete with the radical mechanism.

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