Photochemical and Thermal Decomposition of Bis(3-chloro-2-methylphenyl)diazomethane

Abstract

The reactions of diarylcarbene (2c) generated from the photolytic and thermal decomposition of diaryldiazomethane (1c) were investigated. The effect of steric hindrance in (2c) was insufficient to stabilize the carbene under the photolytic conditions to allow direct dimerization to form the olefin. In the thermal decomposition of (1c), only the azine (3c) was obtained. Both these observations are different from those reported for dimesitylcarbene (2b), and indicate that (2b) undergoes reactions (dependent largely on severe steric hindrance) which are not generally applicable to di-o-tolylcarbene and its derivatives.