MOLECULAR MODELING OF REGIOSELECTIVITY OF GLYCIDIC ACID OPENING REACTIONS BY ALIPHATIC-AMINES

Authors
GROSJEAN F HUCHE M LARCHEVEQUE M LEGENDRE JJ PETIT Y
Citation
F. Grosjean et al., MOLECULAR MODELING OF REGIOSELECTIVITY OF GLYCIDIC ACID OPENING REACTIONS BY ALIPHATIC-AMINES, Tetrahedron, 50(31), 1994, pp. 9325-9334
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
31
Year of publication
1994
Pages
9325 - 9334
Database
ISI
SICI code
0040-4020(1994)50:31<9325:MMOROG>2.0.ZU;2-Z
Abstract
A model for glycidic acids opening reaction by ammonia and amines has been suggested from semi-empiric orbital calculations. It provides a w ay for evaluating the different interactions between the incoming nucl eophile and the oxirane substituents. Steric and coulombic interaction s of the carboxylate in staggered conformation (cis substitution) has a major influence to rationalize experimental regioselectivity.