Terpene amines. III. Synthesis and study of the structure of N-cycloalkyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylamines

Abstract

The reductive amination of cycloalkanones by camphor oxime has been studied. A probable scheme has been put forward for the occurrence of the reaction and the stereochemical composition of its products have been determined. It has been established with the aid of the13C NMR method that the reaction forms a mixture of isomeric optically active N-cycloalkyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylamines with a ratio of the endo to exo isomers of 4:1. The absolute configurations of the amines synthesized have been determined.