The chemistry of terpenes. Part IX. Deamination of the caranamines

Abstract

The products of deamination of (–)-trans-caran-cis-2-amine, (–)-cis-caran-trans-2-amine, (–)-cis-caran-trans-4-amine, (+)-cis-caran-cis-4-amine, (–)-cis-caran-trans-5-amine, and (+)-cis-caran-cis-5-amine have been isolated, and characterised by using chromatographic, chemical, and spectroscopic techniques. The 2- and the 5-amines yielded products expected from the appropriate cyclopropyl-stabilised carbonium ion, whilst the 4-amines afforded a more complex range of products, including the new compounds, R(–)-trans-3-(1-hydroxyethyl)-6,6-dimethylbicyclo[3,1,0]hexane and (+)-3β,7,7-trimethyl-anti-cis-anti-tricyclo[4,1,0,0^2.4]heptane.