Skip to main content
Log in

On the chemistry of pyrrole pigments, XCII: Syntheses of 1,2-bis-pyrrolylethanes

Zur Chemie von Pyrrolpigmenten, 92. Mitt.: Synthesen von 1,2-bis-Pyrrolylethanen

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

Summary

1,2-bis-Pyrrolylethanes are potential synthesis precursors ofb-homorubins. They were synthesized in two ways: by self coupling of a 5-halomethylpyrrole using VCl3/LiAlH4 or by the reduction of 1,2-bis-pyrrolylethenes using Mg-MeOH/Pd-C as catalyst. The yields were 30–40% for the first method and reached 80% for the second one.

Zusammenfassung

1,2-bis-Pyrrolylethane als potentielle Synthesevorstufen vonb-Homorubinen konnten auf zwei Wegen synthetisiert werden. Beim ersten wurden 5-Halogenmethylpyrrole mit VCl3/LiAlH4 dimerisiert; der zweite Weg beruht auf der Reduktion von 1,2-bis-Pyrrolylethenen mit Mg-MeOH/Pd-C als Katalysator. Die Ausbeuten betrugen im ersten Fall um 30–40% und erreichten im zweiten Fall 80%.

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. Part XCI: Falk H., Suste A. (1994) Monatsh. Chem.125: 325

    Google Scholar 

  2. Falk H., Flödl F. (1985) Monatsh. Chem.116: 1177; for a general discussion see also Falk H. (1989) The Chemistry of Linear Oligopyrroles and Bile Pigments. Springer, Wien New York

    Google Scholar 

  3. Falk H., Flödl H. (1986) Monatsh. Chem.117: 57

    Google Scholar 

  4. Wagner U. G., Kratky C., Falk H., Flödl H. (1987) Monatsh. Chem.118: 1185

    Google Scholar 

  5. Falk H., Flödl H., Wagner U. G. (1988) Monatsh. Chem.119: 739

    Google Scholar 

  6. Falk H., Flödl H. (1988) Monatsh. Chem.119: 1155

    Google Scholar 

  7. Eschenmoser A. (1988) Ang. Chem.100: 6

    Google Scholar 

  8. Vogel E., Köcher M., Schmickler H., Lex J. (1986) Ang. Chem.98: 262; Vogel E., Grigat I., Köcher M., Lex J. (1989) Ang. Chem.101: 1687; Vogel E. (1990) Pure. Appl. Chem.62: 557; Will S., Rahbar A., Schmickler H., Lex J., Vogel E. (1990) Ang. Chem.102: 1434; Vogel E., Jux N., Rodriguez-Val E., Lex J., Schmickler H. (1990) Ang. Chem.102: 1431; Vogel E. (1993) Pure & Appl. Chem.65: 143; Sessler J. L., Cyr M. J., Lynch V., McGhee E., Ibers J. A. (1990) J. Am. Chem. Soc.112: 2810; Sessler J. L., Weghorn S. J., Morishima T., Rosingana M., Lynch V., Lee V. (1992) J. Am. Chem. Soc.114: 8306

    Google Scholar 

  9. Falk H., Suste A. (1993) Monatsh. Chem.124: 881

    Google Scholar 

  10. Nogales D. F., Austine D. T., Lightner D. A. (1994) Tetrahedron50: 8579

    Google Scholar 

  11. Warren S. (1982) The Disconnection Approach. Wiley, New York

    Google Scholar 

  12. Fischer H., Orth H. (1968) Die Chemie des Pyrroles, vol I. Johnson Reprint Co., New York, London, p 567

    Google Scholar 

  13. Chen J. T., Yeh Y. S., Sen A. (1989) J. Chem. Soc. Commun.1989: 965

    Google Scholar 

  14. Paine III J. B., Woodward R. B., Dolphin D. (1976) J. Org. Chem.41: 2826

    Google Scholar 

  15. Elli J., Jackson A. H., Jain A. C., Johnson G. W. (1964) J. Chem. Soc.1964: 1935

    Google Scholar 

  16. Ho T. L., Olah G. A. (1977) Synthesis1977: 170

    Google Scholar 

  17. McMurry J. E. (1989) Chem. Rev.89: 1513; Lenoir D. (1989) Synthesis,1989: 883, and Refs. therein

    Google Scholar 

  18. Chen Q.-Q., Yan F., Ma J.-S., Jin S. (1993) Chinese Chem. Lett.4: 576

    Google Scholar 

  19. Profitt J. A., Ong H. H. (1979) J. Org. Chem.44: 3972; Olah G. A., Prakash G. K. S., Arvanaghi M., Bruce M. R. (1981) Angew. Chem.93: 107

    Google Scholar 

  20. Ichimura K., Ichikawa S., Imamura K. (1976) Bull. Chem. Soc. Jap.49: 1157

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, Q.Q., Falk, H. & Micura, R. On the chemistry of pyrrole pigments, XCII: Syntheses of 1,2-bis-pyrrolylethanes. Monatsh Chem 126, 473–479 (1995). https://doi.org/10.1007/BF00813210

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00813210

Keywords

Navigation