Synthesis of α-amino oximes and bis-α-amino oximes from the monoterpene hydrocarbons 3-carene and α-pinene and α,ω-diamines

The reaction of nitroso chlorides of natural monoterpene hydrocarbons, 3-carene and α-pinene, with simple α,ω-diamines (1,2-diaminoethane, 1,3-diaminopropane, piperazine, 1,6-diaminohexane, diethylenetriamine) results in the formation of α-amino oximes and bis-α-amino oximes. The product structures were proved by spectroscopy. The procedures of separation and purification of diamino oximes and diamino dioximes are described. Detailed analysis of the 1H and 13C NMR spectra of the new chiral nitrogen-containing derivatives was carried out.