Intermediates in the decomposition of aliphatic diazo-compounds. Part VI. Thermal decomposition of phenyldiazomethane in acetonitrile

Abstract

The thermal decomposition of phenyldiazomethane in acetonitrile, with and without added water, has been investigated. In anhydrous conditions, benzalazine, cis-stilbene, and trans-stilbene are formed as primary products. Kinetic studies show the reaction to proceed by simultaneous unimolecular and bimolecular processes, the former yielding azine and the stilbenes, while the latter yields azine as a primary product, and stilbenes which may be secondary in origin. In the presence of water, attack of water on the diazo-compound and capture by water of the intermediate phenylcarbene both yield benzyl alcohol.