REACTION OF DIISONITROSOACETONE WITH SULFONYL CHLORIDES.
Quarterly rept. no. 6, Jul-Dec 67,
DELAWARE UNIV NEWARK DEPT OF CHEMISTRY
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This report describes the results obtained on three aspects of the color-forming reaction between diisonitrosoacetone DIA, diethylamine, and tosyl chloride. Further attempts have been made to find a reagent that would increase the color intensity of this reaction. The replacement of diethylamine by other secondary amines generally, but not always, gives lower color intensities, while primary amines give variable results. No significant color intensity increases were observed. The reaction fails when diethylamine is replaced by N-substituted formamides. The replacement of tosyl chloride by p-bromobenzenesulfonyl chloride does not significantly affect the yield, while other compounds tested gave rise to little or no color. The reaction between the solid DIA-diethylamine salt and tosyl chloride vapor occurs readily on silica gel, but much less readily on the other surfaces tested. Methanesulfonyl chloride vapor is slightly less effective than tosyl chloride vapor. The volatility of the amine used seems to have no effect on the color intensity developed. Under certain conditions the color-forming reaction gives a blue or purple solution. An attempt was made to isolate one of the blue compounds present in the complex reaction mixture a substance was isolated and its spectra were recorded, but it was not identified. Author
- Organic Chemistry