Skip to main content
Log in

Thio-analogues of 2-(1H-Heteroarylidene)-1H-indene-1,3(2H)-diones, synthesis and formation of metal complexes

Thio-Analoge von 2-(1H-Heteroaryliden)-1H-inden-1,3(2H)-dionen. Synthese und Bildung von Metallkomplexen

  • Organische Chemie und Biochemie
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

2-(1H-Heteroarylidene)-1H-indene-1,3(2H)-diones were converted into anils and dianils and then into monothio- and dithio-derivatives by treatment with hydrogen sulphide. The 2-pyridinyl monothioderivate was converted into S-alkyl ethers. In contrast with the dione1 the thio-derivatives readily formed isolable complexes with transition metals. Spectroscopic and magnetic data are reported.

Zusammenfassung

2-(1H-Heteroaryliden)-1H-inden-1,3(2 H)-dione wurden in Anile und Dianile und durch anschließende Behandlung mit Schwefelwasserstoff in die entsprechenden Mono- und Di-thio-derivate umgewandelt. Aus den 2-Pyridinyl-monothio-derivaten wurdenS-Alkyl-ether erhalten. Im Gegensatz zum Dion1 bildeten die Thioderivate glatt isolierbare Komplexe mit Übergangsmetallen. Spektroskopische und magnetische Daten werden mitgeteilt.

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

References

  1. Buggle K.,O'Sullivan D.,Ryan N. D., Chem. and Ind.1974, 164.

  2. Buggle K.,Nangle M., Chem. and Ind.1976, 111.

  3. Buggle K.,Power J., J. Chem. Soc. Perkin I1980, 1070.

  4. Eibner A., Lobering M., Chem. Ber.39, 2450 (1906).

    Article  Google Scholar 

  5. Eibner A., Lange O., Ann. Chem.315, 347 (1901).

    Article  Google Scholar 

  6. Batterham T. J., in: N.M.R. Spectra of Simple Heterocycles (Taylor E. C.,Weissberger A., eds.), pp. 47–50. Wiley. 1973.

  7. Dou H. J. M., Hassanaly P., Kister J. Metzger J., Phosphorus and Sulphur3, 355 (1977).

    CAS  Google Scholar 

  8. Freimanis Ya. F., Popelis Yu. Yu., Shrets A. E., Bleidelis Ya. Ya., Kemme A. A., Zhur. Obshehei. Khim.43, 1388 (1973).

    CAS  Google Scholar 

  9. Mondelli R., Merlini L., Tetrahedron22, 3253 (1966).

    Article  CAS  Google Scholar 

  10. Kuhn R., Bahr F., Ann. Chem.516, 155 (1935).

    Article  CAS  Google Scholar 

  11. Manly D., Richardson A., Stock A. M., Tilford C., Amstutz E., J. Org. Chem.32, 373 (1958).

    Article  Google Scholar 

  12. Lombardino J. G., J. Org. Chem.32, 1988 (1967).

    Article  CAS  Google Scholar 

  13. Kacens J.,Neilands O.,Linabergs J., Latv. PSR. Zinat. Akad. Vestis Kyim. Ser.1972, 576.

  14. Amiel J.,Ploquin J.,Sparfel L.,Le Baut G.,Floch R., Bull. Soc. Chim. Fr.1974, 2154.

  15. Friedmanis J., Laurinovics E., Otkrytiya izobret., prom. obratzky, tovarnyl znaki53 (43) 63 (1976); C. A.87, 23054.

    Google Scholar 

  16. Cook J., Martin D., J. Inorg. Nucl. Chem.26, 572 (1964).

    Google Scholar 

  17. Apsit A., Dorfmann K., Oshkaya V., Zhur. Neorg. Khim.19, 182 (1974).

    Google Scholar 

  18. Akbar Ali M., Livingstone S. E., Coord. Chem. Reviews13, 133 (1974).

    Article  Google Scholar 

  19. Adams D. M., Metal Ligand and Related Vibrations, pp. 269 and 316. London: Edward Arnold. 1967.

    Google Scholar 

  20. Maki A., McGarvey B., J. Chem. Phys.29, 31 35 (1958).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buggle, K., Glass, W.K., Nangle, M. et al. Thio-analogues of 2-(1H-Heteroarylidene)-1H-indene-1,3(2H)-diones, synthesis and formation of metal complexes. Monatsh Chem 113, 81–90 (1982). https://doi.org/10.1007/BF00814340

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00814340

Keywords

Navigation