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A combined experimental and theoretical study of the polar [3+2] cycloaddition of electrophilicity activated carbonyl ylides with aldehydes and imines

Authors :
Bentabed-Ababsa, Ghenia
Derdour, Aicha
Roisnel, Thierry
Saez, Jose A.
Perez, Patricia
Chamorro, Eduardo
Domingo, Luis R.
Mongin, Florence
Source :
Journal of Organic Chemistry. March 6, 2009, Vol. 74 Issue 5, 2120-2133
Publication Year :
2009

Abstract

[3+2] Cycloaddition reactions between carbonyl ylides generated from epoxides and aldehydes or imines are studied and used for preparing 2,5-diaryl-1,3-dioxolane-4,4-dicarbonitriles and 2,4-diphenyl-1,3-oxazolidine-5,5-dicarbonitriles. The analysis of the reactivity indexes has shown that the largest electrophilic character of the carbonyl ylides have induced them to act as strong electrophiles in these polar [3+2] cycloaddition reactions.

Details

Language :
English
ISSN :
00223263
Volume :
74
Issue :
5
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.200555003