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Beiträge zur Chemie der Pyrrolpigmente, 50. Mitt.

On the chemistry of pyrrole pigments, L: Phytochrome model studies: The lactam—Lactim equilibrium of the pyrrolidinone fragment of 2,3-dihydrobilatrienes-abc—Protonation equilibria

Phytochrommodellstudien: Das Laktam — Laktimgleichgewicht des Pyrrolidinonfragmentes von 2,3-Dihydrobilatrienen-abc — Protonierungsgleichgewichte

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

Abstract

Using fixed tautomeric structures of 3,4-dihydropyrromethenones and 2,3-dihydrobilatrienes-abc (N- and O-alkylation) a prevalence of the lactam and bis-lactam form over lactimes by several orders of magnitude could be deduced. Although there are complications arising from side reactions of the pyrrolidinone fragment, protonation equilibria provided valuable clues for this result which is nicely complemented by NMR-, IR and UV-VIS data.

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Literatur

  1. 49. Mitt.:Falk H., Kapl G., Müller N., Monatsh. Chem.114, 773 (1983).

    Google Scholar 

  2. Falk H.,Gergely S.,Grubmayr K.,Hofer O., Ann. Chem.1977, 565.

  3. Falk H.,Schlederer T., Ann. Chem.1979, 1560.

  4. Severini-Ricca G., Manitto P., Monti D., Randall E. W., Gazz. Chim. Ital.105, 1273 (1975).

    Google Scholar 

  5. Cullen D. L.,Pepe G.,Meyer E. F.,jr.,Falk H.,Grubmayr K., J. Chem. Soc., Perkin II,1979, 999;Hori A.,Mangani S.,Pepe G.,Meyer E. F. jr.,Cullen D. L.,Falk H.,Grubmayr K., J. Chem. Soc., Perkin II,1981, 1525.

  6. Le Bas G., Allegret A., Mauguen Y., DeRango C., Bailly M., Acta Cryst.B 36, 3007 (1980);Becker W., Sheldrick W. S., Acta Cryst.B 34, 1290 (1978).

    Google Scholar 

  7. Sheldrick W. S., J. Chem. Soc., Perkin II,1976, 1457.

  8. Sheldrick W. S., Becker W., Z. Naturforsch.34 b, 1542 (1979);Kratky C., Jorde C., Falk H., Thirring K., Tetrahedron, im Druck;Dattagupta J. K., Meyer E. F., jr., Cullen D. L., Falk H., Gergely S., Acta Cryst., im Druck.

    Google Scholar 

  9. Falk H., Grubmayr K., Thirring K., Gurker N., Monatsh. Chem.109, 1183 (1978).

    Google Scholar 

  10. Falk H., Grubmayr K., Kapl G., Zrunek U., Monatsh. Chem.113, 1329 (1982).

    Google Scholar 

  11. Yates K., Welch G., Can. J. Chem.50, 1513 (1972).

    Google Scholar 

  12. Kröper H., Houben-WeylVI/2, 560.

  13. Falk H.,Grubmayr K.,Magauer K.,Müller N.,Zrunek U., Isr. J. Chem., im Druck.

  14. Falk H., Grubmayr K., Thirring K., Z. Naturforsch.33 b, 924 (1978).

    Google Scholar 

  15. Falk H.,Müller N., Ergebnisse aus vorläufigenPPP-SCF-LCAO-MO-CI-Rechnungen, die in anderen Zusammenhang mitgeteilt werden.

  16. Loibner H., Seidel G., Chromatographia12, 600 (1979).

    Google Scholar 

  17. Grubmayr K., Monatsh. Chem.113, 1073 (1982).

    Google Scholar 

  18. Falk H., Grubmayr K., Kapl G., Müller N., Zrunek U., Monatsh. Chem.114, 753 (1983).

    Google Scholar 

  19. Atkinson J. H.,Johnson A. W.,Raudenbusch W., J. Chem. Soc. (C),1966, 1155.

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

    Google Scholar 

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Herrn Prof. Dr.J. Derkosch, Universität Wien, zum 60. Geburtstag gewidmet.

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Falk, H., Zrunek, U. Beiträge zur Chemie der Pyrrolpigmente, 50. Mitt.. Monatsh Chem 114, 983–998 (1983). https://doi.org/10.1007/BF00799958

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  • DOI: https://doi.org/10.1007/BF00799958

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