Azatriquinane, azatriquinacene, and a remarkable dimerization product

Article abstract of DOI:10.1016/0040-4039(95)02091-8

Azatriquinane, an amine with a rigid, hemispherical topology, is synthesized in six steps from pyrrole. It is shown to be more basic than quinuclidine, and can be dimerized by N-oxidation and treatment with base to give novel, highly strained heptacycle. Oxidation with chlorine gives an azatriquinacene, a theoretical precursor to diazadodecahedrane.