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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 15 N‐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 .
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Rose et al. (1997) studied this question.
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