Eclipsed Conformation of the Exocyclic N-CH2 Bond in N-Neopentylpiperidines and the Stereodynamic Consequences As Studied by Dynamic NMR Spectroscopy …

JE Anderson, AI Ijeh, C Storch, D Casarini…

Index: Anderson, J. Edgar; Ijeh, Anthony I.; Storch, Christine; Casarini, Daniele; Lunazzi, Lodovico Journal of Organic Chemistry, 1998 , vol. 63, # 10 p. 3310 - 3317

Full Text: HTML

Citation Number: 10

Abstract

The dynamic stereochemistry of a range of N-neopentylpiperidines 1 with an eclipsed N- CH2-t-Bu bond is compared with that of the corresponding range of N-ethylpiperidines 2 with a gauche N-CH2Me bond. By using dynamic NMR spectroscopy, the relative importance of ring inversion, exocyclic bond rotation, and nitrogen inversion are elucidated and barriers are reported and discussed. Minor populations of the neopentyl-axial- ...