Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 0, 1974
Previous Article Next Article

Metal ions and complexes in organic reactions. Part XIX. Response of some N-substituted o-nitrodiphenylamines to cyclisation procedures

Abstract

4-Chloro-4′-methyl-2-nitrodiphenylamine, the corresponding N-methyl- and N-acetyl-compounds, and N-acetyl-4-chloro-2′-methoxy-2-nitrodiphenylamine were compared in their susceptibility to cyclisation when heated (i) alone, (ii) with iron(II) oxalate, or (iii) with triethyl phosphite. The products were phenazine and benzimidazole derivatives and (in one case, with triethyl phosphite) an azepinobenzimidazole derivative. Aromatisation of N-acetyl-5,10-dihydrophenazine was examined. Results from these and preceding investigations of cyclisations through o-nitro-groups are summarised and are discussed in relation to suggested mechanisms. A note on the preparation of o-nitrodiarylamines is included.

Back to tab navigation

Article information


J. Chem. Soc., Perkin Trans. 1, 1974, 1975-1980
Article type
Paper

Metal ions and complexes in organic reactions. Part XIX. Response of some N-substituted o-nitrodiphenylamines to cyclisation procedures

R. G. R. Bacon and S. D. Hamilton, J. Chem. Soc., Perkin Trans. 1, 1974, 1975
DOI: 10.1039/P19740001975

Search articles by author

Spotlight

Advertisements