Reactivity and reaction mechanism for reactions of 1,1 '-(azodicarbonyl) dipiperidine with triphenylphosphines

Reactivity and reaction mechanism for the reactions of 1,1'-(azodicarbonyl) dipiperidine with triphenylphosphines are investigated using kinetic metho d. The cation radical, Ph3P and the anion radical, -N-(N) over bar- are pro duced during the course of the reaction. The cation radical is formed by th e transfer of an electron from phosphorus to the nitrogen atom. The anion r adical is formed by the addition of the one electron to the azo radical. Th e rate constants are decreased by electron withdrawing groups while they ar e increased by electron donating groups present in triphenylphosphine. The electron density increases on nitrogen, while positive charge is developed on phosphorus in the transition state.