New method for the study of reactivity of highly reactive compounds was proposed and applied to determine the effect of substituents in adiazoacetamidines, and -imidales. The introduction of electronreleasing groups to the nitrogen atom of the amidine, and imidate functions was shown to increase the reactivity of the substances studied. The resultsobtained are in good agreement with the heteroelectrocyclic mechanism suggested for the cyclization of these compounds.
INTRODUCTIONDiazo compounds 1-3. bearing C=N-(1). C=S-(2) and C=Sa (3) bonds at the a-position are with a few exceptions very unstable and undergo ringclosure into heterocycles 4-6 under the conditions of their generation. These substances are intermediates in the synthesis of imino(thio, se1eno)ketenes and carbenes, in the preparation of 1.2,3-triazoles 4. thia(se1ena)diazoles 5(6) (1-3) and in rearrangements of I .2,3-triazoles
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