C. Hammer, S. Heller, J. H. Craig
1972
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0
Influential Citations
72
Citations
Quality indicators
Journal
Tetrahedron
Abstract
Abstract 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.