Plyers-shaped diamines II. 3-Amino-2,4-cyclogranatane diastereomers — A study of influence of structure on the properties of diamines

Abstract 3-Amino-2,4-cyclogranatane 3β- and 3α-diastereomers can be synthesized from the corresponding 3β-carbonitriles by a kinetically and a thermodynamically controlled reductive decyanation, respectively. Comparison of both diastereomers with respect to basicity, ionization potentials and behaviour towards oxygen demonstrates the influence of the lone pair - lone pair interaction on the properties of diamines. An X-ray structural analysis of a protonated syn diamine established an N…N -distance of 2.72 A in this new type of compounds.