The chemistry of terpenes. Part V. The preparation of some stereoisomeric caranamines and a study of their conformations

Abstract

Preparative routes to the previously unknown (–)-cis-caran-trans-2-amine, (+)-cis-caran-cis-4-amine, (–)-cis-caran-trans-4-amine, (+)-cis-caran-cis-5-amine, and (–)-cis-caran-trans-5-amine are described, and their configurations are established. The (+)-caranamine prepared by Baeyer and by Menon and Simonsen is probably the enantiomorph of (–)-trans-caran-cis-2-amine now described. The probable conformations of these compounds are discussed in the light of the α-proton band-widths in their n.m.r. spectra.