CHEMISTRY OF TERPENES .9. DEAMINATION OF CARANAMINES

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-hydroxy-ethyl)-6,6-dimethylbicyclo[3,1,0]hexane and (+)-3β,7,7-trimethyl-anti-cis-anti-tricyclo[4,1,0,0 2.4]heptane.