Date of Award
Master of Arts
Masters Thesis-Open Access
When aryl sulfonyl azides substituted with electron releasing groups reacted with N,N-diethylaminoprop-l-yne, the products were found to be l-substituted-4-methyl-5-diethylamino-l,2,3-triazoles. However, when the aryl substituents were electron withdrawing, the products were α-diazo amidines.
In solution, the triazoles were found to exist in equilibrium with an α-diazo tautomer. NMR provided a quantitative method of measuring the percentage of triazole and α-diazo amidine tautomer. The equilibrium was measured in various solvents.
The structures of the compounds were proven by chemical degradation to a N,N-diethyl-N'-arylsulfonyl-propion-amidine.
Stanley, Frederick Warren Jr., "The Reaction of Substituted Benzenesulfonyl Azides with N,N-Diethylaminoprop-l-yne" (1970). Master's Theses. 2992.