Header

UZH-Logo

Maintenance Infos

Addition of carboxylic acidis and cyclic 1,3-diketones to 2-dimethylamino-3,3-dimethyl-1-azirine


Vittorelli, Piero; Heimgartner, Heinz; Schmid, Hans; Hoet, P; Ghosez, Leon (1974). Addition of carboxylic acidis and cyclic 1,3-diketones to 2-dimethylamino-3,3-dimethyl-1-azirine. Tetrahedron, 30:3737-3740.

Abstract

The reaction of 2-dimethylamino-3,3-dimethyl-1-azirine 1 with carboxylic acids 2a-e at room temperature in inert solvents generates rearranged 1:1 adducts in 65-92% yields. These adducts are N-acyl derivatives of 2-amino-N,N-dimethyl-isobutyramide 3a-e resulting from 1,2 addition of the acid followed by 1,2 ring cleavage and transfer of an acyl group. Cyclic enolizable 1,3 diketones 4a-c react similarly with 1 to yield the corresponding rearranged 1:1 adducts 5a-c, whereas acyclic diketones or ethyl acetoacetate are inert under comparable experimental conditions.

Abstract

The reaction of 2-dimethylamino-3,3-dimethyl-1-azirine 1 with carboxylic acids 2a-e at room temperature in inert solvents generates rearranged 1:1 adducts in 65-92% yields. These adducts are N-acyl derivatives of 2-amino-N,N-dimethyl-isobutyramide 3a-e resulting from 1,2 addition of the acid followed by 1,2 ring cleavage and transfer of an acyl group. Cyclic enolizable 1,3 diketones 4a-c react similarly with 1 to yield the corresponding rearranged 1:1 adducts 5a-c, whereas acyclic diketones or ethyl acetoacetate are inert under comparable experimental conditions.

Statistics

Citations

Dimensions.ai Metrics
57 citations in Web of Science®
46 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 01 Dec 2014
0 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1974
Deposited On:01 Dec 2014 16:08
Last Modified:22 Feb 2018 09:58
Publisher:Elsevier
ISSN:0040-4020
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, Institut pour l'Encouragement de la Recherche Scientifique dans l'Industrie et l'Agriculture, Fonds der la Recherche Fondamentale Collective (Belgium)
OA Status:Closed
Publisher DOI:https://doi.org/10.1016/S0040-4020(01)90659-3

Download