Synthesis and NMR investigation of 3,4-diazabicyclo[4.3.0]non-2-ene andN,N'-azo-3-azabicyclo[3.3.0]octane. X-ray crystal structure analysis of a new tetrazene derivative

Autor: H. Delalu, L. Peyrot, Bernard Fenet, B. F. Mentzen, M. Elkhatib
Rok vydání: 1999
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 36:681-686
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570360317
Popis: 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 cyrstal 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.
Databáze: OpenAIRE
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