Nitrosation of m-xylene, anisole, 4-nitrophenyl phenyl ether and toluene in trifluoroacetic acid or in acetic–sulfuric acid mixtures under nitric oxide

Abstract

Nitrosation in trifluoroacetic acid or in acetic–sulfuric acid mixtures is regioselective and accompanying non-selective nitrous acid catalysed nitration can be avoided by purging with nitric oxide.

References

1. D. L. H. Williams, Nitrosation, Cambridge University Press, Cambridge, 1988.
2. B. C. Challis, R. J. Higgins and A. J. Lawson, J. Chem. Soc., Perkin Trans. 2, 1972, 1831; L. Dix and R. B. Moodie, J. Chem. Soc., Perkin Trans. 2, 1986, 1097.
3. R. B. Moodie and B. O'Sullivan, J. Chem. Soc., Perkin Trans. 2, 1995, 205.
4. V. L. Lobachev, O. V. Savsunenko and E. S. Rudakov, Kinet. Catal., 1991, 32, 11.
5. E. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 5573.
6. F. Al-Omran, K. Fujiwara, J. C. Giffney, J. H. Ridd and S. R. Robinson, J. Chem. Soc., Perkin Trans. 2, 1981, 518.
7. F. Radner, A. Wall and M. Loncar, Acta. Chem. Scand., 1990, 44, 152.
8. B. D. Beake and R. B. Moodie, J. Chem. Soc., Perkin Trans. 2, 1995, 1045.
9. A. M. M. Doherty, N. Haine, E. Jones and G. Stedman, J. Chem. Soc., Perkin Trans. 2, 1996, 2045.
10. B. D. Beake and R. B. Moodie, unpublished work.
11. R. B. Moodie, K. Schofield and G. D. Tobin, J. Chem. Soc., Perkin Trans. 2, 1977, 1688.