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Mechanism of benzo-1,2,3,4-tetrazine 1-N-oxide formation
A. M. Churakova,
O. Yu. Smirnova,
Yu. A. Strelenkoa,
S. L. Ioffea,
V. A. Tartakovskya,
Yu. T. Struchkovb,
F. M. Dolgushinb,
A. I. Yanovskyb a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
Аннотация:
Benzo-1,2,3,4-tetrazine 1-
N-oxide formation involves the intramolecular cyclization of 2-(
tert-butyl-
NNO-azoxy)phenyldiazonium tetrafluoroborates and the N→N migration of the
tert-butyl group to afford 2-(
tert-butyl)benzo-1,2,3,4-tetrazinium 4-
N-oxides 3 followed by elimination of the
tert-butyl group. Compounds 3 were hydrolysed to give a new heterocyclic system,
viz. 2-alkyl-6-oxo-2,6-dihydrobenzo-1,2,3,4-tetrazine 4-
N-oxides. For 2-(
tert-butyl)-8-bromo-6-oxo-2,6-dihydrobenzo-1,2,3,4-tetrazine 4-
N-oxide an X-ray diffraction study was carried out.
Язык публикации: английский
DOI:
10.1070/MC1996v006n01ABEH000561
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