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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.