Skip to main content
Log in

Research on the chemistry of phenoxazines

VII. Reactions and properties of resorufin and some of its derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Resorufin (7-hydroxy-3-phenoxazinone) reacts with thiophenols to give 2,8-di(arylthio) derivatives. The site of entry of the nucleophilic residues indicates protonation of resorufin at the ring nitrogen atom. The changes in the absorption spectra of the arylthio derivatives of resorufin in the visible region as a function of the pH of the solution are associated with the acid-base dissociation of these compounds with respect to the hydroxyl group. The ionization constants of some 2,8- and 2,4,6,8-tetrasubstituted resorufin derivatives were measured.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. G. B. Afanas'eva, K. I. Pashkevich, and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., 1246 (1973).

  2. G. B. Afanas'eva, K. I. Pashkevich, I. Ya. Postovskii, V. G. Vykhristyuk, N. P. Shimanskaya, and V. D. Bezuglyi, Khim. Geterotsikl. Soedin., 1344 (1972).

  3. V. Simanek, J. Lasovsky, V. Stuzka, and L. Hruban, Coll. Czech. Chem. Commun., 35, 3064 (1970).

    Google Scholar 

  4. G. B. Afanas'eva and I. Ya. Postovskii, Zh. Obshch. Khim., 34, 3041 (1964).

    Google Scholar 

  5. C. Bodea and J. Silberg, Adv. Heterocycl. Chem., 9, 321 (1968).

    Google Scholar 

  6. H. Musso and H. Matties, Ber., 90, 1914 (1957).

    Google Scholar 

  7. D. P. Sevbo and O. G. Ginzburg, Zh. Organ. Khim., 6, 345 (1970).

    Google Scholar 

  8. P. Weselsky, Ber., 4, 613 (1871).

    Google Scholar 

  9. H. Eichler, J. Prakt. Chem., 139, 113 (1934).

    Google Scholar 

  10. W. Schafer, Progr. Org. Chem., 6, 135 (1964).

    Google Scholar 

  11. A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Methuen (1962).

  12. R. Nietzky and H. Mackler, Ber., 23, 720 (1890).

    Google Scholar 

  13. Organic Syntheses, Vol. 2, Wiley.

  14. E. Ruzicka and J. Jurina, Monatsh., 97, 129 (1966).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for communication VI.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 348–353, March, 1974.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Afanas'eva, G.B., Viktorova, T.S., Pashkevich, K.I. et al. Research on the chemistry of phenoxazines. Chem Heterocycl Compd 10, 302–306 (1974). https://doi.org/10.1007/BF00472415

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00472415

Keywords

Navigation