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Doyle, M.P, Siegfried, B. and Dellaria Jr., J.F. (1977) Alkyl Nitrite-Metal Halide Deamination Reactions. 2. Substitutive Deamination of Arylamines by Alkyl Nitrites and Copper(II) Halides. A Direct and Remarkably Efficient Conversion of Arylamines to Aryl Halides. The Journal of Organic Chemistry, 42, 2426-2429.
http://dx.doi.org/10.1021/jo00434a017

has been cited by the following article:

• TITLE: An Efficient and Green Route to Synthesize Azo Compounds through Methyl Nitrite

  AUTHORS: Kejie Cai, Hongqiang He, Yuwei Chang, Weiming Xu

  KEYWORDS: Methyl Nitrite, Substituted Benzenamine, Diazotization, Azo Coupling, Dyes, Pigments, Environmentally Benign, Toxicological

  JOURNAL NAME: Green and Sustainable Chemistry, Vol.4 No.3, August 5, 2014

  ABSTRACT: A clean preparation of aryl diazonium ions using methyl nitrite is described. Further reaction of the aryl diazonium ions with substituted benzenamine, substituted phenol and nathphol in deferent kinds of diazotization has been developed. In order to improve the water-solubility of the products, azo coupling reactions of sodium sulfanilate hydrochloride diazonium ions were also performed. The procedures are easy operations, environmentally benign conditions and high yields of the products with potential use as azo-dyes and pigments. Furthermore, no nitrous acid is produced during the diazotization which avoided the formation of dark decomposition products of the corresponding aromatic amine. Proposed mechanism is presented according to our procedure.