Tetrahedron p. 9325 - 9334 (1994)
Update date:2022-07-30
Topics:
Grosjean, F.
Huche, M.
Larcheveque, M.
Legendre, J. J.
Petit, Y.
A model for glycidic acids opening reaction by ammonia and amines has been suggested from semi-empiric orbital calculations.It provides a way for evaluating the different interactions between the incoming nucleophile and the oxirane substituents.Steric and coulombic interactions of the carboxylate in staggered conformation (cis substitution) has a major influence to rationalize experimental regioselectivity.
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Doi:10.1016/0039-128X(64)90075-3
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