Journal of Heterocyclic Chemistry p. 681 - 686 (1999)
Update date:2022-08-11
Topics:
Delalu
Elkhatib
Peyrot
Fenet
Mentzen
3,4-Diazabicyclo[4.3.0]non-2-ene and N,N'-azo-3-azabicyclo[3.3.0]octane are the main products of the oxidation of N-amino-3-azabicyclo[3.3.0]octane by chloramine. These new compounds have been isolated and characterized. A structural study has been performed with the goal of establishing the cis- trans configuration at the bicyclic junction. Multinuclear proton decoupling carried out on the endocyclic hydrazone has allowed the determination of the coupling constant of the bridgehead hydrogens. A low temperature conformational study shows splitting of the 13C signal of the carbon atom located α with respect to the ammonia nitrogen. This result, consistent with a cis structure, was confirmed by a nmr analysis conducted on the solid tetrazene derivative. The X-ray data collection on a single crystal of the tetrazene has permitted us to determine the crystallographic properties of this compound. Data processing by direct methods reveals that the geometry of the molecule presents a cis configuration for the bicyclic bridge link and a trans one for the azo group, confirming thus the main results obtained by nmr studies.
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