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

Citation
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
Citations number
54
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
6
Year of publication
2000
Pages
1037 - 1043
Database
ISI
SICI code
1434-193X(200003):6<1037:OONABM>2.0.ZU;2-B
Abstract
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.