| Abstrakt: |
The cyanoethylation reactions of 1-phenyl-1,2,4-triazoline-3-thione (I) and of 1-phenyl-1,2,4,-triazoline-5-thione (II) have been studied. The cyanoethylation of I forms only S-cyanoethyl derivates,and the cyanoethylation of II only N-cyanoethyl derivatives. The structures of the reaction products were confirmed by UV spectroscopy and by independent synthesis. On the basis of a quantum-mechanical analysis of the compounds, their tautomeric forms, and the assumed primary reaction products, it has been concluded that the mechanism of the cyanoethylation and transcyanoethylation reactions of these heterocyclic thioamides is a common one. |
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