Synthesis and structural studies of symmetric and unsymmetric adamantylmethyleneazines

The synthesis and spectroscopic properties (1H, 13C and 15N NMR, in solution and in the solid state) of six new 1-adamantylmethylene azines are reported. The crystal and molecular structures of 1-adamantylcarbaldehyde azine and 1-adamantyl methyl ketone azine, which exist in the solid state in the E,E-configuration, were determined by x-ray analysis. The geometric characteristics of the azine central bridge and the preferred configuration with regard to it (E,E, E,Z or Z,Z) were investigated by means of the crystallographic data retrieved from the Cambridge Structural Database and ab initio quantum chemical calculations.