Determination of the conformations and relative configurations of exocyclic amines

The conformations and relative configurations of 20 amines, classified according to the following labeling scheme, were analyzed. Series a comprised compounds derived from N ‐(1‐phenylethyl)cyclohexanamine, b comprised derivatives of N ‐[1‐(naphthalen‐2‐yl)ethyl]cyclohexanamine, c comprised derivatives of N ‐(diphenylmethyl)cyclohexanamine, and d comprised derivatives of N ‐(propan‐2‐yl)cyclohexanamine. The compounds were labeled as follows: 1 indicates cyclohexanamine, 2 indicates 2‐methylcyclohexanamines, 3 indicates 3‐methylcyclohexanamines, 4 indicates 4‐methylcyclohexanamines, and 5 indicates 4‐ tert ‐butylcyclohexanamines. These compounds were prepared without the use of stereoselective induction and, therefore, all expected stereoisomers were observed. Structural assignments were established by 1 H, 13 C, and 15 N NMR. Copyright © 2010 John Wiley & Sons, Ltd.