On the thermal decomposition of diazirines

Abstract

Kinetic data for the thermal decomposition of 3-phenyl-3-trifluoromethyldiazirine, 1-phenyl-2,2,2-trifluorodiazoethane, and 3-methyl-3-vinyldiazirine are reported. Detailed analysis of the previously studied diazirine decompositions suggest a mechanism in which a carbene–nitrogen complex is formed as the first intermediate. This complex, depending on the relative rates and stabilities of intermediates and products, may collapse to a diazo compound and/or form a free carbene. Thus for different diazirines the isomerization to a diazo compound may or may not be observed.