Synthesis and properties of 3‐nitrosocarbazole | Zendy

Kyziol Janusz B. | Zendy

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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.

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