Mechanistic studies on azoalkane cation radical decomposition

Article abstract of DOI:10.1016/S0040-4039(00)60014-X

We report on the oxidative decomposition of two azoalkanes, azo-bis-2-methyl-2-propane and 3,3,6,6-tetramethyl-1,2-diazacyclohex-2-ene. These azoalkane cation radicals decompose at rates ≥ 10¹⁸ times faster than their neutral precursors. This can be attributed to a decrease of ≥ 24 kcal/mol in the C-N bond dissociation energy on oxidation.