Synthesis and Characterization of N‑Unsubstituted 2- and 3‑Furanimines

N-unsubstituted 2-furanmethanimine and 3-furanmethanimine are the simplest derivatives of an imine family containing numerous drugs. They have been prepared in the gas phase by dehydrocyanation of the corresponding α-aminonitriles, characterized by IR and NMR spectroscopy at low temperature and used in transimination reactions. The kinetic stability of the furanaldimines lies between that of alkylated and arylated derivatives, demonstrating the role played by the substituent. The triethylborane complexes of the aldimines were synthesized by reacting the corresponding nitriles with superhydride.