In contrast to the addition of iodine azide to cyclooctene (1) or 1,3-
cyclooctadiene (5), its reaction with 1,5-cyclooctadiene (12) leads ma
inly to the surprisingly stable tetraazido-substituted 2-tetrazene 14.
The structure of this was established by N-15-NMR studies and an X-ra
y structural analysis. Treatment of 14 with hydrochloric acid yields t
he diazido-substituted 9-azabicyclo[3.3.1]nonane 20.