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Nucleophilic displacement of N-benzyl groups: effect of pyridinium on rates and mechanism
Journal article   Peer reviewed

Nucleophilic displacement of N-benzyl groups: effect of pyridinium on rates and mechanism

Alan R. Katritzky, Giuseppe Musumarra and Kumars Sakizadeh
Tetrahedron letters, Vol.21(28), pp.2701-2703
1980
DOI: https://doi.org/10.1016/S0040-4039(00)78584-4

Abstract

Steric acceleration by α-substituents in pyridine leaving groups is quantitatively assessed. Constraint of α-phenyls to near planarity forms superior leaving groups for S N2 displacements. α-t-Butyl groups significantly increase S N1 dissociation.

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