Synthesis and structural studies of symmetric and unsymmetric adamantylmethyleneazines

The synthesis and spectroscopic properties (H-1, C-13 and N-15 NMR, in solu tion and in the solid state) of six new 1-adamantylmethylene azines are rep orted. The crystal and molecular structures of 1-adamantylcarbaldehyde azin e and 1-adamantyl methyl ketone azine, which exist in the solid state in th e E,E-configuration, were determined by x-ray analysis. The geometric chara cteristics 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 crystallo graphic data retrieved from the Cambridge Structural Database and ab initio quantum chemical calculations. Copyright (C) 1999 John Wiley & Sons, Ltd.