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The mechanism of aromatic nitration by tetranitromethane

✍ Scribed by Neil S. Isaacs; Obaid Hassan Abed

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 218 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87462-6

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✦ Synopsis

Aromatm nitrations by tetramtromethane are shown to be photochemically initiated and are believed to proceed via trinitromethyl nitrite. Tetranitromethane ( TNM) has become known as a mild and somewhat unpredictable nitrating agent of aromatic rings. It will give, for example, some 70% of 3-nitro-4-dimethylamlnotoluene when treated with p-toluldme at room temperature 1 . Azulene is nitrated in the 1-position m good yield 2 and several nucleophflic heterocycles react ltkewise 394 . Phenols, as phenoxlde ions, are &rated m variable yield at posltlons typical of an electrophllm attack although frequently accompamed by products of radical couplmg. P-cresol,

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