Abstract
The condensation of 3.4-dimethyl-3-pyrrolin-2-one with p-methyl-, p-chloro-benzaldehyde and ferrocenealdehyde yields theZ-andE-isomers of the corresponding condensates. Due to kinetic control theZ-isomers are obtained almost exclusively in this reaction. TheE-isomers of the two firstmentioned products can be produced by photochemical isomerization. The structures (tautomeric forms) and configurations of the isomers were established by the Lanthanide-induced-shift-technique and by evaluating the Nuclear-Overhauser-Effect.
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H. Falk, O. Hofer undH. Lehner, Mh. Chem.105, 169 (1974).
H. Falk, O. Hofer undH. Lehner, Mh. Chem.105, 366 (1974).
H. Falk, S. Gergely undO. Hofer, Mh. Chem.105, 853 (1974).
H. Falk undO. Hofer, Mh. Chem.105, 995 (1974).
H. Falk, S. Gergely undO. Hofer, Mh. Chem.105, 1004 (1974); in dieser Mitt. wurden ebenfalls die “shift”-Werte für ein Molverhältnis 1∶0,33 angegeben, jedoch irrtümlich als 1∶1-Daten zitiert.
H. Falk, S. Gergely undO. Hofer, Mh. Chem.105, 1019 (1974).
H. Falk undO. Hofer, Mh. Chem.106, 97 (1975).
W. Rüdiger, Fortschr. Chem. Org. Naturst.29, 61 (1971).
A. Gossauer, Die Chemie der Pyrrole. Berlin-Heidelberg-New York: Springer. 1974.
A. Gossauer undH. H. Inhoffen, Ann. Chem.738, 18 (1970).
H. Plieninger, H. Bauer undA. R. Katritzky, Ann. Chem.654, 165 (1962).
K. Yamada, Y. Togawa, T. Kato undY. Hirata, Tetrahedron27, 5445 (1971).
A. J. Fry, R. S. H. Liu undG. S. Hammond, J. Amer. Chem. Soc.88, 4781 (1966);M. Kikuchi, K. Kikuchi undH. Kokobun, Bull. Chem. Soc. Jap.47, 1331 (1974).
R. Eberhardt, H. Lehner undK. Schlögl, Mh. Chem.104, 1409 (1973).
L. Pauling, The Nature of the Chemical Bond. Ithaca: Cornell Univ. Press. 1960.
M. R. Willcott III, R. E. Lenkinski undR. E. Davis, J. Amer. Chem. Soc.94, 1742 (1972); für die Überlassung eines Programm-decks des PDIGM-Programms danken wir Herrn Prof.R. E. Davis sehr herzlich.
W. C. Hamilton, Acta Cryst.18, 502 (1965);R. E. Davis undM. R. Willcott III, J. Amer. Chem. Soc.94, 1744 (1972).
J. H. Atkinson, R. S. Atkinson undA. W. Johnson, J. Chem. Soc.1964, 5999.
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8. Mitt.:H. Falk undO. Hofer, Mh. Chem.106, 115 (1975).
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Falk, H., Grubmayr, K. & Hofer, O. Beiträge zur Chemie der Pyrrolpigmente, 9. Mitt.: Bildung, Struktur und Konfiguration vonZ- undE-Arylmethyliden-3,4-dimethyl-3-pyrrolin-2-onen. Monatshefte für Chemie 106, 301–312 (1975). https://doi.org/10.1007/BF00914522
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DOI: https://doi.org/10.1007/BF00914522