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Beiträge zur Chemie der Pyrrolpigmente, 76. Mitt.: Die Synthese von symmetrisch substituierten 2,2′-Bipyrrolen durch oxidative Kupplung

On the chemistry of pyrrole pigments, LXXVI: A synthesis of symmetrically substituted 2,2′-bipyrroles by oxidative coupling

  • Organische Chemie Und Biochemie
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Abstract

A method for the synthesis of symmetrically substituted 2,2′-bipyrroles using the oxidation of α-unsubstituted pyrrole derivatives—in analogy to the oxidative coupling of phenols—is presented together with four examples. The mechanistic implications are discussed.

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Literatur

  1. 75. Mitt:Falk H, Medinger W, Müller N (1988) Monatsh Chem 119: 113

    Google Scholar 

  2. Eichinger D, Falk H (1987) Monatsh Chem 118: 255

    Google Scholar 

  3. Falk H, Flödl H (1985) Monatsh Chem 116: 1177

    Google Scholar 

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

    Google Scholar 

  5. Williams RP, Hearn WR (1967) In:Gottlieb D, Shaw PD (eds) Biosynthesis. Springer, Berlin Heidelberg New York (Antibiotics, vol 2, pp 410–451)

    Google Scholar 

  6. Siehe z. B.:Jackson AH, Smith KM (1973) In:Simon A (ed) The total synthesis of natural products, vol 1. Wiley-Interscience, New York, p 144. Vgl. dazu auch die kürzlich dargestellten Porphycene:Vogel E, Kocher M, Schmickler H, Lex J (1986) Angew Chem 98: 262

    Google Scholar 

  7. Andre JM, Vercauteren DP, Street GB, Bredas JL (1984) J Chem Phys 80: 5643;Orti E, Sanchez-Marin J, Tomas F (1986) Theor Chim Acta 69: 41

    Google Scholar 

  8. Grigg R, Johnson AW, Wasley JWF (1963) J Chem Soc 1963: 359;Grigg R, Johnson AW (1964) J Chem Soc 1964: 3315

    Google Scholar 

  9. Z. B.:Rapoport H, Castagnol N (1962) J Am Chem Soc 84: 2178

    Google Scholar 

  10. Hinz W, Jones A, Patel SU, Karatza M (1986) Tetrahedron 42: 3753

    Google Scholar 

  11. Musso H (1963) Angew Chem 75: 965

    Google Scholar 

  12. Taylor WS, Battersby AR (1967) Oxidative coupling of phenols. Dekker, New York

    Google Scholar 

  13. Barton DHR, Deflorin AM, Edwards OE (1956) J Chem Soc 1956: 530;Kharasch MS, Yoshi BS (1957) J Org Chem 22: 1439

    Google Scholar 

  14. Gossauer A (1974) Die Chemie der Pyrrole. Springer, Berlin Heidelberg New York

    Google Scholar 

  15. Jones RA, Bean GP (1977) The chemistry of pyrroles. Academic Press, London

    Google Scholar 

  16. Diaz AF, Kanazawa KK, Gardini GP (1979) J Chem Soc Chem Commun 1979: 635

    Google Scholar 

  17. Kuhn R, Osswald G (1956) Chem Ber 89: 1423

    Google Scholar 

  18. Bauer H (1967) Chem Ber 100: 1704

    Google Scholar 

  19. Bauer H (1968) Chem Ber 101: 1286

    Google Scholar 

  20. Pfeiffer G, Bauer H (1980) Ann Chem 1980: 564

    Google Scholar 

  21. Rotermund GW, Seubert R (1975) Houben-Weyl 5/1b: 673

    Google Scholar 

  22. Bauer VJ, Clive DLJ, Dolphin D, Paine III JB, Harris FL, King MM, Loder J, Wang SC, Woodward RB (1983) J Am Chem Soc 105: 6429

    Google Scholar 

  23. Bender CO, Bonnett R (1968) J Chem Soc 1968: 2526

    Google Scholar 

  24. Fischer H, Höfelmann H (1983) Ann Chem 533: 213

    Google Scholar 

  25. Badger GM, Ward AD (1964) Austral J Chem 17: 649

    Google Scholar 

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Authors and Affiliations

  1. Institut für Chemie, Johannes-Kepler-Universität Linz, A-4040, Linz, Austria

    Heinz Falk & Heinz Flödl

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  1. Heinz Falk
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  2. Heinz Flödl
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Falk, H., Flödl, H. Beiträge zur Chemie der Pyrrolpigmente, 76. Mitt.: Die Synthese von symmetrisch substituierten 2,2′-Bipyrrolen durch oxidative Kupplung. Monatsh Chem 119, 247–252 (1988). https://doi.org/10.1007/BF00809598

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  • DOI: https://doi.org/10.1007/BF00809598

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