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 Å in this new type of compounds.
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