Nitration in the Carbazole Series, II | Zendy

Kyziol Janusz B. | Zendy; Daszkiewicz Zdislaw | Zendy

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Nitration in the Carbazole Series, II

Author(s) -

Kyziol Janusz B.,

Daszkiewicz Zdislaw

Publication year - 1985

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.198519850705

Subject(s) - nitration , carbazole , chemistry , acetic acid , nitro , sulfuric acid , alkali metal , medicinal chemistry , organic chemistry , alkyl

9‐Nitrocarbazole ( 1 ) was prepared and rearranged to give a mixture of 1‐nitro‐ ( 2 ) and 3‐nitrocarbazole ( 3 ) in the same ratio as observed in the case of the carbazole nitration. The evidence for the formation of 1 during the nitration of carbazole in acetic acid is given. The formation of C ‐nitro compounds during methylation of the 1,3,6,8‐tetrachlorocarbazole/1,3,6,8‐tetrachloro‐9‐nitrocarbazole complex can be explained by an alkali‐catalysed nitramine rearrangement. The mechanism of this rearrangement is discussed.

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