Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
---Excess N-benzyl aziridine (1) reacts with I2 to afford dimer 2, tetramer 3, benzaldehyde (4), and iodoamine 5. The reaction is interpreted as occurring by both electron transfer (ET) and heterolytic mechanisms. An ET mechanism is substantiated for the oxidation by I2 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 boundaries to the competition between the ET and heterolytic mechanisms. For the reaction of 1 with 5 a reaction scheme is proposed; in a particular case, a pseudo-first order kinetic law is followed.
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