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Synthesis and properties of 3‐nitrosocarbazole
Author(s) -
Kyziol Janusz B.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220531
Subject(s) - chemistry , disproportionation , chloride , medicinal chemistry , methylation , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , gene
The synthesis of 3‐nitrosocarbazole (I) by the Fischer‐Hepp rearrangement of 9‐nitrosocarbazole has been described. The resistance of I to oxidation provides evidence that it cannot be the intermediate in the conversion of 9‐nitrosocarbazole to the C‐nitro compounds. It has also been shown that I and its derivatives cannot be synthesized by the action nitrosyl chloride on carbazoles. Methylation of I yields 9‐methyl‐3‐nitrosocarbazole, 9,9′‐dimethyl‐3‐azocarbazole and 9,9′‐dimethyl‐3‐azoxycarbazole as the main products. The mechanism of this disproportionation process has been proposed. The spectral data of I are given.