Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Oxidation of N-Alkylhydroxylamines. II. Reaction of N-Alkylhydroxylamines with tert-Butylhydroperoxide
HIROTERU SAYOSHIGEKO OZAKIMASAICHIRO MASUI
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1972 Volume 20 Issue 5 Pages 1012-1016

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Abstract
The title reaction in benzene gives a C-nitroso compound, tert-butanol and presumably water according to the equation : RNHOH+tert-BuOOH→R-N=O+tert-BuOH+H2O During the reaction electron spin resonance (ESR) spectra due to [chemical formula]·is observed. In the presence of a large excess of N-alkylhydroxylamine, tert-butylhydroperoxide decomposes through a 1 : 2 complex with N-alkylhydroxylamine and the activation energy of the reaction is about 12 kcal. Unless N-alkylhydroxylamine is present in fairly large excess, tert-butylhydroperoxide decomposes by direct homolysis : tert-BuOOH→tert-BuO·+HO· and the activation energy is about 33 kcal.
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© The Pharmaceutical Society of Japan
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