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.
Similar content being viewed by others
Literatur
49. Mitt.:Falk H., Kapl G., Müller N., Monatsh. Chem.114, 773 (1983).
Falk H.,Gergely S.,Grubmayr K.,Hofer O., Ann. Chem.1977, 565.
Falk H.,Schlederer T., Ann. Chem.1979, 1560.
Severini-Ricca G., Manitto P., Monti D., Randall E. W., Gazz. Chim. Ital.105, 1273 (1975).
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.
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).
Sheldrick W. S., J. Chem. Soc., Perkin II,1976, 1457.
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.
Falk H., Grubmayr K., Thirring K., Gurker N., Monatsh. Chem.109, 1183 (1978).
Falk H., Grubmayr K., Kapl G., Zrunek U., Monatsh. Chem.113, 1329 (1982).
Yates K., Welch G., Can. J. Chem.50, 1513 (1972).
Kröper H., Houben-WeylVI/2, 560.
Falk H.,Grubmayr K.,Magauer K.,Müller N.,Zrunek U., Isr. J. Chem., im Druck.
Falk H., Grubmayr K., Thirring K., Z. Naturforsch.33 b, 924 (1978).
Falk H.,Müller N., Ergebnisse aus vorläufigenPPP-SCF-LCAO-MO-CI-Rechnungen, die in anderen Zusammenhang mitgeteilt werden.
Loibner H., Seidel G., Chromatographia12, 600 (1979).
Grubmayr K., Monatsh. Chem.113, 1073 (1982).
Falk H., Grubmayr K., Kapl G., Müller N., Zrunek U., Monatsh. Chem.114, 753 (1983).
Atkinson J. H.,Johnson A. W.,Raudenbusch W., J. Chem. Soc. (C),1966, 1155.
Paine III J. B., Woodward R. B., Dolphin D., J. Org. Chem.41, 2826 (1976).
Author information
Authors and Affiliations
Additional information
Herrn Prof. Dr.J. Derkosch, Universität Wien, zum 60. Geburtstag gewidmet.
Rights and permissions
About this article
Cite this article
Falk, H., Zrunek, U. Beiträge zur Chemie der Pyrrolpigmente, 50. Mitt.. Monatsh Chem 114, 983–998 (1983). https://doi.org/10.1007/BF00799958
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00799958