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Origin of the reactivity differences of substituted aziridines: Cn vs CC bond breakages

Authors :
Paasche, Alexander
Arnone, Mario
Fink, Reinhold F.
Schirmeister, Tanja
Engels, Bernd
Source :
Journal of Organic Chemistry. August 7, 2009, Vol. 74 Issue 15, 5244-5249
Publication Year :
2009

Abstract

The reaction courses of possible ring-opening reactions accompanied by the attack of a nucleophile for different substituent patterns of the aziridine are examined. The results have helped in understanding the mechanisms of different ring-opening reactions and have explained how the kinetics and thermodynamics of the reaction are affected by substituents, which has predicted substitution patterns that steer the reaction course to either CN or CC bond cleavage.

Details

Language :
English
ISSN :
00223263
Volume :
74
Issue :
15
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.208159981