Transanular Interactions in Difunctional Medium Rings, 6. Spectroscopic Investigations of Bicyclic Amino Ketones

The endo‐7‐(aminomethyl)bicyclo[3.3.1]nonan‐3‐ones 1–4 with a primary, secondary, or tertiary amino group have been synthesized, and their tendency to form the corresponding tricyclic amino carbinols has been investigated by theoretical (MMX, AM1) and experimental (PE, 13C‐NMR spectroscopy) methods. Comparison of the characteristic spectroscopic properties of 1–4 with those of the isochromophoric monofunctional compounds 7–11 indicates that 1 and 2 form mixtures with the tricyclic isomers 5 and 6, respectively, whereas 3 and 4 show no interactions between the amino and the carbonyl group in the solely present bicyclic structures.