Synthesis of a tetraazido-substituted 2-tetrazene from 1,5-cyclooctadiene and iodine azide

Article abstract of DOI:10.1002/jlac.199719970219

In contrast to the addition of iodine azide to cyclooctene (1) or 1,3-cyclooctadiene (5), its reaction with 1,5-cyclooctadiene (12) leads mainly to the surprisingly stable tetraazido-substituted 2-tetrazene 14. The structure of this was established by ¹⁵N-NMR studies and an X-ray structural analysis. Treatment of 14 with hydrochloric acid yields the diazido-substituted 9-azabicyclo[3.3.1]nonane 20. VCH Verlagsgesellschafi mbH, 1997.