Date of Award
Bachelor of Science
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.
Kennicott, Helen Carol, "The synthesis and decomposition of O-substituted phenylhydroxylamines" (1976). Honors Theses. 1828.