Abstract
The effect of N-substitution on the elimination reactions of benzimidazolines is studied making use of 1-benzyl-3-methyl (I), 1-substituted benzyl-3-methyl (II) and 1-substituted benzyl-3-beazyl (III)-2-aryl benzimidazolines. The results of pyrolysis of I and II show that of the two substituents on the nitrogens, the benzyl or substituted benzyl group is eliminated in preference to the methyl group and the nature or the position of the aromatic substituent has no effect on the course of elimination. It appears that the superior stability of the eliminating radical, benzyl or substituted benzyl group due to resonance, determines the course of reaction. In type (III) compounds, the course of the elimination reaction is determined by the relative stability of the benzyl and substituted benzyl radicals.
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Satyanarayana Reddy, P., Veeranagaiah, V. & Ratnam, C.V. Studies in the formation of heterocyclic rings containing nitrogen. Proc. Indian Acad. Sci. 81, 132–136 (1975). https://doi.org/10.1007/BF03051138
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DOI: https://doi.org/10.1007/BF03051138