IUCr journals

3,3-Pentamethylenediaziridine

Acta Cryst. (2004). E60, o1921–o1922 [doi:10.1107/S1600536804023888]

[crystal structure] A view of the unit cell, showing the disordered hydrogen-bond network along the b axis. Hydrogen bonds are shown as dashed lines. H and C atoms are shown as small spheres of arbitrary radii. H atoms attached to C atoms have been omitted.
N,N-unsubstituted diaziridines are very useful moieties, being precursors by oxidation to diazirines, more stable structural isomers of diazo compounds, that can be used as carbene precursors. Surprisingly, only crystal structures of either N-substituted or N-complexed diaziridines compounds have been reported so far. The title compound is the first free N,N-unsubstituted 3,3-dialkyldiaziridine to be structurally characterized. The analysis was only successfully achieved using the sealed capillary method. The crystal structure indicates the presence of intermolecular N-H…N hydrogen bonds, resulting in a three-dimensional network.

A. B. Charette, C. Legault and F. Bélanger-Gariépy