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Nitration in the Carbazole Series, II

✍ Scribed by Kyziol, Janusz B. ;Daszkiewicz, Zdislaw

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
581 KB
Volume
1985
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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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