STEREOCHEMISTRY OF ALPHA-AMINO OXIMES FROM THE MONOTERPENE HYDROCARBONS CAR-3-ENE, LIMONENE AND ALPHA-PINENE

The conformation and configuration of the alpha-ainino oximes derived from the terpene hydrocarbons car-3-ene, limonene and alpha-pinene have been determined by n.m.r. spectroscopy (high-field H-1 n.m.r., C-13 n.m.r., INADEQUATE technique), molecular mechanics calculations and X-ray crystallographic analysis. The crystal structure of (1S,3S,6R)-3-dimethylamino-caran-4-one (E)-oxime has been determined by X-ray diffraction; crystals are orthorhombic, space group P2(1)2(1)2(1) with a 11.421(2), b 13.223(2), c 16.992(4) angstrom, Z 8. Refinement on 1730 observed reflections measured with Cu K-alpha radiation converged at R 0.053.