Aryl azides (p-XC6H4N3) decompose in boiling phenyl isocyanate to give mainly 1-phenyl-3-phenyl-carbamoyl-2-oxo-1,3-dihydrobenzimidazoles and azo-compounds. In some cases, however (X = Ac, CO2Me, or CN) work-up in methanol solution produces methyl N-arylcarbamates (p-XC6H4NHCO2Me) indicative of the formation of substituted isocyanates (p-XC6H4NCO) during thermolysis. A mechanistic rationale is offered.
D. I. Patel and R. K. Smalley, J. Chem. Soc., Perkin Trans. 1, 1984, 2587 DOI: 10.1039/P19840002587
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