Monatshefte fur Chemie p. 1113 - 1120 (1994)
Update date:2022-08-11
Topics:
Delalu, H.
El Khatib, M.
Marchand, A.
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.The reaction leads to the transient formation of a saturated bicyclic aminonitrene (diazene).At pH > 13, the diazene undergoes an intramolecular rearrangement to afford a hydrazone.At pH < 9, a white solid is formed resulting from the dimerization of the molecular and protonated forms of the aminonitrene.At intermediate pH-values, a mixture of both species is obtained.They have been isolated and characterized by UV, GC/MS, IR, and 1H/13C NMR.A reaction mechanism is proposed. - Keywords.Synthesis; 3,4-Diazabicyclo<4,3,0>non-2-ene; N,N'-Azo-3-azabicyclo<3,3,0>octane; Diazene; Hydrazine; NMR.
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