M. Caproiu et al., Oxidation of N-benzyl aziridine by molecular iodine: Competition of electron transfer and heterolytic pathways, EUR J ORG C, (6), 2000, pp. 1037-1043
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.