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Issue 4, 1999
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Kinetics and mechanism of nitrosation of toluene, o-xylene, and m-xylene in trifluoroacetic acid, or in acetic–sulfuric acid mixtures, under nitric oxide

John H. Atherton,  Roy B. Moodie  and  Darren R. Noble 

Abstract

The title reactions give good yields with m-xylene, and modest yields with toluene and o-xylene which are successfully directly nitrosated for the first time. The advantages of purging with nitric oxide are demonstrated and discussed. The kinetics have been successfully interpreted in terms of a mechanism in which both the aromatic substrate and the nitrosoaromatics form, reversibly, complexes with nitrosonium ion. The nitrosoaromatics are unstable under the acid conditions and the method is successful only because of the protective complexation with the nitrosonium ion.

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Article type: Paper
DOI: 10.1039/A900476I
Citation: J. Chem. Soc., Perkin Trans. 2, 1999,0, 699-706
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    Kinetics and mechanism of nitrosation of toluene, o-xylene, and m-xylene in trifluoroacetic acid, or in acetic–sulfuric acid mixtures, under nitric oxide

    J. H. Atherton, R. B. Moodie and D. R. Noble, J. Chem. Soc., Perkin Trans. 2, 1999, 0, 699
    DOI: 10.1039/A900476I

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