Reactions of β-substituted amines—II: Nucleophilic displacement reactions on 3-chloro-1-ethylpiperidine☆☆☆

Add time:08/30/2019    Source:sciencedirect.com

Synthetic, kinetic and optical activity studies have established that 3-chloro-1-ethylpiperidine undergoes nucleophilic displacement reactions in solution by a two-step, neighboring group participation mechanism. Nitrogen displaces chloride internally, to give an ambident bicyclic aziridinium ion which then reacts with nucleophiles to give pyrrolidine and piperidine isomers. The aziridinium ion. 1-ethyl-1-azoniabicyclo[3.1.0]hexane perchlorate, has been synthesized separately.

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