Skip to main content
SpringerLink
Log in

Reaction of π-deficient aromatic heterocycles with ammonium polyhalides III. Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides

Reaktion elektronenarmer aromatischer Heterocyclen mit Ammoniumpolyhalogenverbindungen, 3. Mitt. Halogenierung von Phenothiazin-5-oxid mit Benzyltriethylammoniumpolyhalogeniden

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides (BTEA) under mild conditions afforded chloro- and bromophenothiazines as well as a few unexpected products e.g. 1,3,7,9-tetrachloro-phenothiazin-5-oxide, 7,3′-dibromo-3, 10′-diphenothiazinyl tribromide, and 7,3′-dichloro-3,10′-diphenothiazinyl tetrachloroiodate. A new charge-transfer complex of phenothiazine-5-oxide with bromine is reported.

Zusammenfassung

Halogenierung von Phenothiazin-5-oxid mit Benzyltriethylammoniumhalogeniden (BTEA) unter milden Bedingungen ergab neben Chlor- und Bromphenothiazinen einige unerwartete Reaktionsprodukte wir z.B. 1,3,7,9-Tetrachlorphenothiazin-5-oxid, 7,3′-Dibrom-3,10′-diphenothiazinylbromid und 7,3′-Dichlor-3,10′-diphenothiazinyltetrachloriodat. Außerdem wird über einencharge-transfer-Komplex von Phenothiazin-5-oxid mit Brom berichtet.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Custelceanu R, Vlassa M, Silberg IA, Fărcas IS, Culea M, Szöke M (1997) Heterocyclic Commun (in press)

  2. Vlassa M, Silberg IA, Custelceanu R (1995) Synthetic Commun25: 3493

    Google Scholar 

  3. Kajigaeshi S, Kakinami T, Okamoto T, Nakamura H, Fujikawa M (1987) Bull Chem Soc Jpn60: 4187

    Google Scholar 

  4. Okamoto T, Kakniami T, Fujimoto H, Kajigaeshi S (1991) Bull Chem Soc Jpn64: 2566

    Google Scholar 

  5. Page HJ, Smiles S (1910) J Chem Soc97: 1115

    Google Scholar 

  6. Gillman H, Eisch J (1955) J Am Chem Soc77: 3862

    Google Scholar 

  7. Schmaltz AC, Burger A (1954) J Am Chem Soc76: 5455

    Google Scholar 

  8. Antonov DS (1957) Compt Rend Acad Bulg Sci10: 21; (1958) Chem Abstr52: 6357 g

    Google Scholar 

  9. Zhuravlev SV, Skorodumov VA (1956) Zh Org Khim1: 202

    Google Scholar 

  10. Bodea C, Silberg IA (1968) Advances in Heterocyclic Chemistry, vol 9. Academic Press, New-York, pp 322–460

    Google Scholar 

  11. Bodea C, Fărcăsan V, Oprean, I (1963) Studii Cercet Chim (Cluj, Romania)14: 173; (1964) Chem Abstr61: 9493 e

    Google Scholar 

  12. Gillman H, Diehl JW (1961) J Org Chem26: 2938

    Google Scholar 

  13. Tsujino Y, Nishikida K, Naito T (1970) Nippon Kagaku Zasshi91: 1080; (1971) Chem Abstr74: 125598 k

    Google Scholar 

  14. Diudea M, Silberg IA (1982) J Prakt Chem324: 769

    Google Scholar 

  15. Hanson P, Norman ROC (1973) J Chem Soc Perkin Trans II, 264

  16. Kemp TJ, Moore P, Quick GR (1980) J Chem Soc Perkin Trans II, 291

  17. Bhat SN, Kuroda H (1973) Bull Chem Soc Jpn46: 3585

    Google Scholar 

  18. Doi S, Matsunaga Y (1975) Bull Chem Soc Jpn48: 3447

    Google Scholar 

  19. Hiroyoshi K (1969) Japan Pat 69 14, 718; (1969) Chem Abstr71: 86087j

  20. Silberg IA (1970) Thesis, Cluj, Romania

  21. Craig JC, Rogers WA, Warwick CP (1955) Austral J Chem8: 252

    Google Scholar 

  22. Bodea C, Terdic M, Silber IA (1960) Liebigs Ann Chem631: 194

    Google Scholar 

  23. Bodea C, RĂileanu M (1958) Studii Cercet Chim (Cluj, Romania)9: 159; (1961) Chem Abstr55: 15497 e

    Google Scholar 

  24. Bodea C, RĂileanu M (1959) Liebigs Ann Chem621: 88

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry and Chemical Engineering, Department of Organic Chemistry, Babes-Bolyai University, RO-3400, Cluj-Napoca, Romania

    R. Custelceanu, M. Vlassa & I. A. Silberg

Authors
  1. R. Custelceanu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Vlassa
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. A. Silberg
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Custelceanu, R., Vlassa, M. & Silberg, I.A. Reaction of π-deficient aromatic heterocycles with ammonium polyhalides III. Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides. Monatsh Chem 128, 919–925 (1997). https://doi.org/10.1007/BF00807101

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807101

Keywords

Search

Navigation