Kinetics and Mechanisms of Nucleophilic Displacements with Heterocycles as Leaving Groups. 2. N-Benzylpyridinium Cations: Rate Variation with Steric Effects in the Leaving Group

Article abstract of DOI:10.1021/jo00332a013

N-Benzyl groups are transferred to piperidine from pyridinium ions by unimolecular S_N1 and/or bimolecular S_N2 mechanisms.Steric acceleration by α-phenyl groups is reduced by an adjacent β-methyl group but increased by constraining th