4.6- Dinitro-2- benzotriazole 1-oxide

Dinitrohydroxykenzophenyltriazole, C, 2H7NgOg mw 301.22, N 23.25% not found in Beil, but its isomer 2-Phenyl-4,6-dinitro-benzotriazole- 1-oxide, It yel crysts, mp 195 6°, is listed in Beil 26,50... 

Die Verbindungen sind auch direkt aus 4,6-Dinitro-benzofurazan-l-oxid mit N-Formyl-anili-nen in alkalischer Losung zuganglich. Benzofurazan-l-oxid selbst liefert keine 4-Anilino-benzo-furazane, sondern man erhalt Benzotriazol-1-oxide78. 

Beim Bestrahlen von l-(2-Nitro-pheny])- bzw. l-(2,4-Dinitro-phenyl)-lH-pyrazolen(253,7 nm, 300nm und 355 nm) werden 2-(2-Acyl-ethenyl)-benzotriazol-l-oxide als (.E/Z)-Isome-ren-Gemische gebildet z. B2363 ... 

This study reports on the reactions of ambident nucleophiles with electron-deficient nitroaromatic and heteroaromatic substrates anionic complex formation or nucleophilic substitution result. Ambident behavior is observed in the case of phenoxide ion (O versus C attack) and aniline (N versus C attack). O or N attack is generally kinetically preferred, but C attack gives rise to stable thermodynamic control. Normal electrophiles such as 1,3,5-trinitrobenzene or picryl chloride are contrasted with superelectrophiles such as 4,6-dinitrobenzofuroxan or 4,6-dinitro-2-(2,4,6-trinitrophenyl)benzotriazole 1-oxide (PiDNBT), which give rise to exceptionally stable a complexes. Further interesting information was derived from the presence in PiDNBT of two electrophilic centers (C-7 and C-l ) susceptible to attack by the ambident nucleophilic reagent. The superelectrophiles are found to exhibit lesser selectivity toward different nucleophilic centers of ambident nucleophiles compared with normal electrophiles. 

Dinitro-2-(2,4,6-trinitrophenyl)benzotriazole 1-Oxide (PiDNBT) as an Ambident Superelectrophile... 

---