The Stability and Conformation of the 1,3,6,8-Tetraazatricyclo[4.4.1.13,8]dodecane System: the Structure of the Condensation Product of 1,2-Diaminocyclohexane and Formaldehyde

Abstract

The condensation of d,1-trans-1,2-diaminocyclohexane with formaldehyde gives a pentacyclic molecule based on the 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane nucleus. This was shown to have S4 symmetry by 1H n.m.r. and an X-ray analysis showed crystals to be orthorhombic, Fddd, a = 12.02, b = 19.25, c = 12.90 Å. The symmetry of the compound in the crystal was D2d due to a disordered arrangement and structure analysis was carried out to R = 0.166. When optically active diamine was used as starting material, the analogous reaction did not occur and this was attributed to strain in the tricyclic system. The conformation of the molecule is related to those of similar compounds as found by X-ray analysis.