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Reactions of 3-Amino-2H-azirines with NH-Acidic Compounds


Heimgartner, Heinz (1981). Reactions of 3-Amino-2H-azirines with NH-Acidic Compounds. Israel Journal of Chemistry, 21:151-156.

Abstract

3-Dimethylamino-2,2-dimethyl-2H-azirine (1) reacts with a number of NH-acidic compounds to give adducts of interesting structural variety. In analogy to the reaction of OH-acidic substrates, the reaction mechanism can be understood to proceed via initial protonation of the aminoazirine, subsequent attack of the nitrogen nucleophile on the iminiumaziridine and ring expansion of the three-membered ring to form a zwitterionic intermediate. Depending very much on the charge-distribution delivered by the variety of substituents, this zwitterionic intermediate is going to be stablised by different routes, e.g. water elimination, ring enlargement or rearrangement, to yield new N-heterocyclic compounds.

Abstract

3-Dimethylamino-2,2-dimethyl-2H-azirine (1) reacts with a number of NH-acidic compounds to give adducts of interesting structural variety. In analogy to the reaction of OH-acidic substrates, the reaction mechanism can be understood to proceed via initial protonation of the aminoazirine, subsequent attack of the nitrogen nucleophile on the iminiumaziridine and ring expansion of the three-membered ring to form a zwitterionic intermediate. Depending very much on the charge-distribution delivered by the variety of substituents, this zwitterionic intermediate is going to be stablised by different routes, e.g. water elimination, ring enlargement or rearrangement, to yield new N-heterocyclic compounds.

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Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1981
Deposited On:24 Jul 2014 07:27
Last Modified:05 Apr 2016 17:58
Publisher:Wiley-Blackwell
ISSN:0021-2148

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