Abstract
Starting from optically active methylferrocene-α- and-β-carboxylic acids (1 a and1 b) of known absolute configuration and enantiomeric purity about 15 chiral ferrocenes (of each isomeric series—α and β) were obtained by suitable ligand transformations. Thereby (almost) all possible chiral combinations of the ligands CH3, COOH (COO−), COOCH3, C≡N and NH2 (NH3 +) were accessible which are necessary for a potential test of approximations of chirality functions for compounds with basic symmetry C5v. The chiroptical properties of these disubstituted ferrocenes are recorded.
Preliminary tests using a shortened Ansatz revealed large discrepancies between calculated (χ) and found [M]D-values. Possible reasons for this failure are discussed.
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Literatur
E. Ruch undA. Schönhofer, Theoret. Chim. Acta19, 225 (1970);
E. Ruch, Acc. Chem. Research5, 49 (1972).
W. J. Richter, B. Richter undE. Ruch, Angew. Chem.85, 21 (1973); Internat. Ed.12, 30 (1973).
E. Ruch, W. Runge undG. Kresze, Angew. Chem.85, 10 (1973); Internat. Ed.12, 20 (1973).
H. Neudeck undK. Schlögl, Chem. Ber., im Druck.
R. Eberhardt, Dissertation, Universität Wien, 1973.
H. Egger undA. Nikiforov, Mh. Chem.99, 2311 (1968) und100, 1069 (1969);H. Gowal undK. Schlögl, Mh. Chem.98, 2302 (1967) und99, 267, 972 (1968) sowie darin zitierte Arbeiten.
Siehe z. B.:K. Schlögl in: Topics in Stereochemistry (N. L. Allinger undE. L. Eliel, Hrsg.)1, 39. New York: Interscience, 1967;K. Schlögl, Pure Appl. Chem.23, 413 (1970) und darin zitierte Arbeiten.
K. Schlögl undH. Falk in: Methodicum Chimicum (K. Niedenzu undH. Zimmer, Hrsg.), Band8, S. 433. Stuttgart: G. Thieme, 1974 bzw. S. 469. New York: Academic Press. 1976.
H. Falk, K. Schlögl undW. Steyrer, Mh. Chem.97, 1029 (1966);
G. Haller undK. Schlögl, Mh. Chem.98, 603 (1967).
G. Haller undK. Schlögl, Mh. Chem.98, 2044 (1967).
H. Falk undK. Schlögl, Mh. Chem.102, 33 (1971).
P. Reich-Rohrwig undK. Schlögl, Mh. Chem.99, 1752 (1968);R. Eberhardt, C. Glotzmann, H. Lehner undK. Schlögl, Tetrahedron Lett.1974, 4365.
H. Falk, H. Lehner, J. Paul undU. Wagner, J. Organometal. Chem.28, 115 (1971).
A. Fatiadi, Synthesis1976, 65 (vgl. Ref. 27-29 bzw. 26 auf S. 66).
E. Vowinkel undJ. Bartel, Chem. Ber.107, 1221 (1974).
H. Falk, G. Haller undK. Schlögl, Mh. Chem.98, 592 (1967).
H. Lehner undK. Schlögl, Mh. Chem.101, 895 (1970).
K. Schlögl undM. Walser, Mh. Chem.100, 840 (1969).
R. S. Cahn, C. K. Ingold undV. Prelog, Angew. Chem.78, 413 (1966); Internat. Ed.5, 385 (1966).
W. C. Hamilton, Statistics in Physical Science, S. 157–162. New York: Ronald Press. 1964.
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61. Mitt. über Ferrocenderivate
39. Mitt.:A. Meyer, H. Neudeck undK. Schlögl, Chem. Ber.110, 1403 (1977).
60. Mitt.:V. Rapić, K. Schlögl undB. Steinitz, J. Organometal. Chem.94, 87 (1975).
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Rapić, V., Schlögl, K. & Steinitz, B. Stereochemie von Metallocenen, 40. Mitt.. Monatshefte für Chemie 108, 767–780 (1977). https://doi.org/10.1007/BF00898040
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DOI: https://doi.org/10.1007/BF00898040