REACTION OF DIISONITROSOACETONE WITH SULFONYL CHLORIDES.
Abstract
This report describes the attempts made to find a reagent that would increase the color intensity developed in the reaction involving the formation of 3-diethylamino-4-pyrazolone-1-oxide from diisonitrosoacetone, diethylamine, and p-tolunesulfonyl chloride. It was found that p-phenylenediamine, p-aminophenol, quinone, and 1,4-naphthoquinone altered the reaction path, while ascorbic acid markedly inhibited the formation of the pyrazolone. Cupric sulfate and ferrous sulfate prevented the occurrence of the reaction, whereas hydrazobenzene, hydroquinone, hydrogen peroxide, cumene hydroperoxide, hydrazine, 1,2-dimethylhydrazine, o-phenylenediamine, isopropanol, butanethiol, cysteine, or benzoyl peroxide had no effect on the overall color-forming reaction. The color intensity developed depends upon the amount of secondary amine added to the reaction, and the pyrazolone is destroyed by excess of a primary or secondary amine, ammonia, or sodium hydroxide. The exclusion of aerial oxygen affects the reaction. Open-chain secondary amines react with DIA and tosyl chloride to give strongly colored solutions, but piperidine is less reactive, morpholine much less so, and diphenylamine does not react at all. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Sep 18, 1967
- Accession Number
- AD0820660
Entities
People
- Edward S. Wilks
- William A. Mosher
Organizations
- University of Delaware