4-Aziadamantan-1-amine: synthesis, reactions and cyclodextrin complexes

A new and potentially therapeutic diazirine, 4-aziadamantan-1-amine, was synthesized. Structural characterization also included single crystal X-ray diffraction analysis. Photolysis of the title compound in the solid phase afforded an azine. In contrast, pyrolysis in the gas phase gave two intramolecular carbene insertion products in a 4:1 ratio. A rationale for the observed diastereoselectivity is offered based upon ab initio calculations. Finally, inclusion compounds of the title compound with α- and β-cyclodextrin were prepared. A 2:1 complex bearing two hosts was formed with α-cyclodextrin and a 1:1 complex was obtained with β-cyclodextrin. The association constants were determined via induced circular dichroism (ICD) analysis.