Abstract
Nitrosonium ethyl sulfate reacts withO-alkylphenols andN,N-dialkylanilines to give the corresponding 4-nitrosoarenes. The reaction is not accompanied by side processes characteristic of common nitrosating agents. Diazotization of primary aromatic amines with nitrosonium ethyl sulfate yields stable diazonium salts, which are promising reagents for organic synthesis.
Similar content being viewed by others
References
The Chemistry of Nitro and Nitroso Groups, Part 1, Ed. H. Feuer, Interscience, New York, 1969.
B. C. Challis, R. J. Higgins, and A. J. Lowson,J. Chem. Soc., Perkin Trans. 1, 1972,12, 1831.
D. L. H. Williams,Nitrosation, Cambridge University Press, Cambridge, 1988, 214.
N. S. Zefirov, Yu. A. Lapin, E. E. Nesterov, and N. V. Zyk,Zh. Org. Khim., 1993,29, 1489 [Russ. J. Org. Chem., 1993,29, (Engl. Transl.)].
N. S. Zefirov, N. V. Zyk, Yu. A. Lapin, E. E. Nesterov, and B. I. Ugrak,J. Org. Chem., 1995,60, 6771.
N. V. Zyk, E. E. Nesterov, A. N. Khlobystov, and N. S. Zefirov,Izv. Akad. Nauk, Ser. Khim., 1996, 1322 [Russ. Chem. Bull., 1996,45, 1259 (Engl. Transl.)].
H. H. Hodgson and D. E. Nicholson,J. Chem. Soc., 1941,8, 470.
Organic Synthesis, Collect. Vol. 2, Ed. A. Blatt, Wiley, New York, 1946.
K. Lutz and J. B. Lytton,J. Org. Chem. 1937,2, 68.
P. Ramart-Lucas and M. M. Martynoff,Bull. Soc. Chim. France, 1949, 53.
Dtsch. Reichspatent No. 3 253 306, 1920.
B. V. Gidaspov and E. Yu. Belyaev,Aromaticheskie nitrozosoedineniya [Aromatic Nitroso Compounds], Khimiya, Leningrad, 1991, 106 (in Russian).
J. D. Piper and W. R. Brode,J. Am. Chem. Soc., 1935,57, 135.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 510–513, March, 1999.
Rights and permissions
About this article
Cite this article
Zyk, N.V., Nesterov, E.E., Khlobystov, A.N. et al. Nitrosation of arenes with nitrosonium ethyl sulfate. Russ Chem Bull 48, 506–509 (1999). https://doi.org/10.1007/BF02496170
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02496170