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A selective synthesis of enamines versus aziridines

✍ Scribed by Dalila Belei; Elena Bicu; Peter G. Jones; M. Lucian Birsa

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
138 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of 10‐azidoacetyl‐10__H__‐phenothiazine with olefinic dipolarophiles depends on the reaction temperature. In refluxing toluene, a mixture of enamine and aziridine is formed in 3:1 ratio. The reaction mechanism appears to involve a Michael‐type addition of the nucleophilic N^1^ azide atom to the olefinic double bond. In chloroform, a cycloaddition reaction takes place with the formation of a 4,5‐dihydro‐1,2,3‐triazole. The heating of dihydrotriazoles in toluene is accompanied by nitrogen elimination leading to a mixture of enamine and aziridine in 1:3 ratio. J. Heterocyclic Chem., 2011.

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## Abstract The photoelectron (PE.) spectra of __N__‐vinylaziridine (**1**) and some methyl and ethyl substituted derivatives are discussed in the light of quantum‐chemical model calculations using the PRDDO SCF method. All aziridine enamines are found to exist as equilibrium mixtures of variable c