Symmetry loss in piperidine and morpholine by nitrogen coordination.

Abstract

We describe herein different degrees of asymmetry in hur N-adducts !3-6 obtained by reaction of mrpholine 1 and piperidine 2 with boranetetrahydrofurane (BGTHF) 3 a n d 4 or with pentadienyltricarbonylmangahese 6 and 6 a s evidenced by both the 'H and '% nuclear magnetic resonance spectra (NMR). The ability of both Lewis acids to coordinate to the nitrogen atom in piperidine and morpholine serves to illustrate certain principles of symmetry, conformational analysia, and NMR spectroscopy.