REACTION OF DIISONITROSOACETONE WITH SULFONYL CHLORIDES.
Summary rept. Jul 65-Dec 67,
DELAWARE UNIV NEWARK DEPT OF CHEMISTRY
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This report summarizes the work carried out on the synthesis and structure determination of diisonitrosoacetone DIA and on the color-forming reaction between DIA, p-toluenesulfonyl chloride, and various amines and amides. Extensive evidence suggests that the DIA molecule exists primarily in the syn-syn conformation, although this has not been finally proved. The reaction between DIA, diethylamine, and tosyl chloride has been studied extensively, and is known to be complex several products are formed, one of which has been identified as red 3-diethylamino-4-pyrazolone-1-oxide. Free radicals have been detected in the reaction solution. Attempts have been made to increase the color intensity of the solution by the addition of specific compounds, but results were disappointing. The substitution of diethylamine by other amines gives a variety of results, while the replacement of tosyl chloride by other similarity-acting reagents does not raise the intensity of color developed. The color-forming reaction takes place readily when tosyl chloride vapor is brought into contact with a silica gel surface previously impregnated with DIA and diethylamine. The other surfaces tested were much less suitable. Modification of experimental procedure in the color-forming reaction gives a blue or purple solution. This complex reaction mixture was shown to contain at least five colored compounds and two colorless compounds. One blue compound was isolated, but it was not identified. Author
- Organic Chemistry