Homolytic reactions of aromatic side-chains. Part V. Reactions with nitrogen-centred free radicals

Abstract

The thermal decomposition of some 2-tetrazene derivatives and of tetrasubstituted hydrazines gives substituted amino-radicals which react by dimerisation, disproportionation, or by abstraction of hydrogen atoms from suitable donors. The relative importance of these modes of reaction depends upon the structure of the radicals. Phenyl substituents suppress hydrogen abstraction, and dimerisation occurs only with dimethylamino-radicals. Relative rates of abstraction of α-hydrogen atoms from the side-chains of some toluene derivatives by dimethylamino-radicals have been measured, and indicate that these radicals are slightly electrophilic.