Oxidation of N-benzyl aziridine by molecular iodine: Competition of electron transfer and heterolytic pathways

Excess N-benzyl aziridine (1) reacts with Ia to afford dimer 2, tetramer 3, benzaldehyde (4), and iodoamine 5. The reaction is interpreted as occurrin g by both electron transfer (ET) and heterolytic mechanisms. An ET mechanis m is substantiated for the oxidation by I, of dimer 2 and tetramer 3, both being substrates easier to oxidise by electron abstraction than 1. Several auxiliary reactions were performed on 1 in order to firmly establish the bo undaries to the competition between the ET and heterolytic mechanisms. For the reaction of 1 with 5 a reaction scheme is proposed; in a particular cas e, a pseudo-first order kinetic law is followed.