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Thermal fragmentation and rearrangement of some N-phenylbenzamide oxime dervatives II. Synthesis of benzimidazoles

Research Authors
Abd El-Aal M. Gaber, Hussni A. Muathen, Layla A. Taib
Research Abstract

Thermolysis of N-phenylbenzamide oximes I, II and III (R = Cl, NO2 and OCH3) under nitrogen gives rise
to benzimidazoles as the major products (45–52%), in addition to benzonitrile, arylamines, benzoic acid,
phenols, benzanilides, 2-phenyl benzoxazoles and carbazoles. In the presence of naphthalene, I gave
- and -naphthols beside the previous products. Also heating of I under reflux boiling tetralin lead to
the formation of 1-hydroxytetralin, -tetralone and 1,1-bitetralyl as the major products. The isolated
products have been interpreted in the terms of a free radical mechanism involving the homolysis of N–O
and/or C–N bonds.

Research Department
Research Journal
Journal of Analytical and Applied Pyrolysis
Research Vol
Vol.91
Research Year
2011
Research Pages
PP.119–124