Gmelin Handbook of Inorganic Chemistry
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Gmelin Handbook of Inorganic Chemistry 8th Edition Organametallic Compounds in the Gmelin Handbook The following listing indicates in which volumes these compounds are discussed or are referred to: Ag Silber B 5 (1975) Au Organogold Compounds (1980) Bi Bismut-Organische Verbindungen (1977) Co Kobalt-Organische Verbindungen 1 (1973), 2 (1973), Kobalt Erg.-Bd. A (1961), B 1 (1963), B 2 (1964) Cr Chrom-Organische Verbindungen (1971) Cu Organacopper Compounds 1 (1985), 2 (1983) Fe Eisen-Organische Verbindungen A 1 (1974), A 2 (1977), A 3 (1978), A 4 (1980), A 5 (1981 ), A 6 (1977), A 7 (1980), Organoiron Compounds A 8 (1986) present volume, Eisen-Organische Verbindungen B 1 (partly in English; 1976), B 2 (1978), B 3 (partly in English; 1979), B 4 (1978), B 5 (1978), Organoiron Compounds B 6 (1981 ), B 7 (1981 ), B 8 to B 10 (1985), B 11 (1983), B 12 (1984), Eisen-Organische Verbin dungen C 1 (1979), C 2 (1979), Organoiron Compounds C 3 (1980), C 4 (1981), C 5 (1981), C 7 (1986), and Eisen B (1929-1932) Hf Organahafnium Compounds (1973) Nb Niob B 4 (1973) Ni Nickel-Organische Verbindungen 1 (1975), 2 (1974), Register (1975), Nickel B 3 (1966), and C 1 (1968), C 2 (1969) Np, Pu Transurane C (partly in English; 1972) Pt Platin C (1939) and D (1957) Ru Ruthenium Erg.-Bd. (1970) Sb Organoantimony Compounds 1 (1981), 2 (1981), 3 (1982) Sc, Y, 0 6 (1983) La to Lu Sn Zinn-Organische Verbindungen 1 (1975), 2 (1975), 3 (1976), 4 (1976), 5 (1978), 6 (1979), Organotin Compounds 7 (1980), 8 (1981), 9 (1982), 10 (1983), 11 (1984), 12 (1985) Ta Tantal B 2 (1971) Ti Titan-Organische Verbindungen 1 (1977), 2 (1980), 3 (1984), 4 and Register (1984) U Uranium Suppt. Vol. E 2 (1980) V Vanadium-Organische Verbindungen (1971), Vanadium B (1967) Zr Organozirconium Compounds (1973) Gmelin Handbook of lnorganic Chemistry 8th Edition Gmelin Handbuch der Anorganischen Chemie Achte, völlig neu bearbeitete Auflage Prepared Gmelin-lnstitut für Anorganische Chemie and issued by der Max-Planck-Gesellschaft zur Förderung der Wissenschaften Director: Ekkehard Fluck Founded by Leopold Gmelin 8th Edition 8th Edition begun under the auspices of the Deutsche Chemische Gesellschaft by R. J. Meyer Continued by E. H. E. Pietsch and A. Kotowski, and by Margot Becke-Goehring Springer-Verlag Berlin Heidelberg GmbH 1986 Gmelin-lnstitut für Anorganische Chemie der Max-Planck-Gesellschaft zur Förderung der Wissenschaften ADVISORY BOARD Dr. J. Schaafhausen, Chairman (Hoechst AG, Frankfurt/Main-Höchst), Dr. G. Breil (Ruhr chemie AG, Oberhausen-Holten), Dr. G. Broja (Bayer AG, Leverkusen), Prof. Dr. G. Fritz (Universität Karlsruhe), Prof. Dr. N. N. Greenwood (University of Leads), Prof. Dr. R. Hoppe (Universität Gießen), Dr. H. Moell (BASF-Aktiengesellschaft, Ludwigshafen), Prof. Dr. H. Nöth (Universität München), Prof. Dr. G. zu Putlitz (Universität Heidelberg), Prof. Dr. A. Rabenau (Max-Planck-lnstitut für Festkörperforschung, Stuttgart), Prof. Dr. Dr. H. A. Staab (Präsident der Max-Planck-Gesellschaft, München), Prof. Dr. Dr. h. c. mult. G. Wilke (Max-Planck-lnstitut für Kohlenforschung, Mülheim/Ruhr) DIRECTOR DEPUTY DIRECTOR Prof. Dr. Dr. h. c. Ekkehard Fluck Dr. W. Lippert CHIEF EDITORS Dr. K.-C. Buschback - Dr. H. Bergmann, F. Füssel, Dr. H. Katscher, Dr. R. Keim, Dipl.-Phys. D. Koschel, Dr. U. Krüerke, Dr. H. K. Kugler, Dr. P. Marlet, Dr. E. Schleitzer-Rust, Dr. A. Slawisch, Dr. F. Schröder, Dr. B. v. Tschirschnitz-Geibler, Dr. R. Warncke STAFF D. Barthel, Dr. N. Baumann, Dr. W. Behrendt, Dr. L. Berg, Dipl.-Chem. E. Best, Dipl.-lng. V. A. Chavizon, E. Cloos, Dipl.-Phys. G. Czack, I. Deim, Dipl.-Chem. H. Demmer, R. Dowideit, Dipl. Chem. M. Drößmar, M. Engels, Dr. H.-J. Fachmann, Dr. J. Faust, Dr. W.-D. Fleischmann, V. Frick, Dr. R. Froböse, G. Funk, Dipl.-lng. N. Gagel, E. Gerhardt, Dr. U. W. Gerwarth, M.-L. Gerwien, Dipl.-Phys. D. Gras, C. Gorr, H. Hartwig, Dipl.-Min. H. Hein, G. Heinrich-Sterzel, H.-P. Hente, H. W. Herold, U. Hettwer, Dr. I. Hinz, Dr. W. Hoffmann, Dipl.-Chem. K. Holzapfel, Dr. S. Jäger, Dr. J. von Jouanne, H.-G. Karrenberg, Dipl.-Phys. H. Keller-Rudek, Dr. L. Kießling, Dipl.-Phys. E. Koch, Dr. E. Koch, Dipl.-Chem. K. Koeber, Dipl.-Chem. H. Köttelwesch, R. Kolb, E. Kranz, Dipl.-Chem. I. Kreuzbichler, Dr. A. Kubny, Dr. P. Kuhn, Dr. W. Kurtz, M. Langer, Dr. A. Leonard, Dipl.-Chem. H. List, H. Mathis, E. Meinhard, Dr. M. Mirbach, Dr. U. Neu-Becker, K. Nöring, Dipl.-Chem. R. Nohl, Dipl.-Min. U. Nohl, Dr. W. Petz, I. Rangnow, Dipl.-Phys. H.-J. Richter-Ditten, Dipl.-Chem. H. Rieger, B. Riegert, E. Rieth, A. Rosenberger, Dr. B. Roth, E. Ru dolph, G. Rudolph, Dipl.-Chem. S. Ruprecht, Dr. R. C. Sangster, V. Schlicht, Dipl.-Chem. D. Schneider, Dipl.-Min. P. Schubert, A. Schwärzet, Dipl.-lng. H. M. Somer, E. Sommer, M. Teichmann, Dr. W. Töpper, Dipl.-lng. H. Vanecek, Dipl.-Chem. P. Velic, Dipl.-lng. U. Vetter, H.-M. Wagner, Dipl.-Phys. J. Wagner, R. Wagner, Dr. E. Warkentin, Dr. B. Wöbke, K. Wolff, U. Ziegler CORRESPONDENT MEMBERS OF THE SCIENTIFIC STAFF Dr. J. R. Clark, Dr. D. B. Gerth, Dr. J. L. Grant, Dr. K. Rumpf, Dr. K. Swars, Dr. U. Trobisch, Dr. B. Vance EMERITUS MEMBER OF THE INSTITUTE Prof. Dr. Dr. E. h. Margot Backe CORRESPONDENT MEMBERS OF THE INSTITUTE Prof. Dr. Hans Bock Prof. Dr. Dr. Alois Haas, Sc. D. (Cantab.) Gmelin Handbook of lnorganic Chemistry 8th Edition Fe Organoiron Compounds Part A Ferrocene 8 Mononuclear Disubstituted Ferrocene Derivatives with C-, H-, and 0-Containing Substituents (continued from "Ferrocene" 7) With 14 illustrations AUTHOR Marianne Drößmar-Wolf EDITOR Adolf Slawisch FORMULA INDEX Edgar Rudolph CHIEF EDITOR Adolf Slawisch Springer-Verlag Berlin Heidelberg GmbH 1986 LlTERATURE CLOSING DATE: 1984 IN SOME CASES MORE RECENT DATA HAVE BEEN CONSIDERED Library of Congress Catalog Card Number: Agr 25-1383 ISBN 978-3-662-08852-4 ISBN 978-3-662-08850-0 (eBook) DOI 10.1007/978-3-662-08850-0 This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, reuse of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks. Under § 54 of the German Copyright Law where copies are made for other than private use, a fee is payable to "Verwertungsgesellschatt Wort", Munich. © by Springer-Verlag Berlin Heidelberg 1985 Originally published by Springer-Verlag Berlin Heidelberg New York Tokyo in 1985 Softcover reprint of the hardcover 8th edition 1985 The use of registered names, trademarks, etc., In this publicatian does not imply, even in the absence of a specific slatement, that such names are exempt from the relevant protective laws and regulatiQns and therefore free for general usa. Preface "Organoiron Compounds" A, Ferrocene 8 systematically covers the Literature through the end of 1984 and even includes some references published more recently. A formula index for the volumes "Organoiron Compounds" A, Ferrocene 7 and 8 provides ready access to the compounds covered. This volume continues the description of ferrocenes FeC10H8R1R2 in which at least R1 contains C, H, and 0. The description of these type of compounds started in "Organoiron Compounds" A, Ferrocene 7 (with alcohols and phenols, their esters, ethers and acetones, and aldehydes). Series Aso far comprises volumes A 1 to A 8, and it has been surveyed in the preface to A 7 (1980). The data in tables are given in abbreviated form without dimensions; for dimensions, explanations, and further abbreviations used, see p. VIII (next page). Additional remarks, if necessary, are given in the headings of the tables. Frankfurt Adolf Slawisch November 1985 VIII Remarks on Abbreviations and Dimensions Many compounds in this volume are presented in tables in which numerous abbreviations are used, and the dimensions are omitted for the sake of conciseness. This necessitates the following clarification: Temperstures are given in oc, otherwise K stands for Kelvin. Abbreviations used with temperatures are m.p. for melting point, b.p. for boiling point, dec. for decomposition, and sub!. for sublimation. The solvent in parentheses following the m.p. is the solvent from which the compound is recrystallized. NMR represents nuclear magnetic resonance. Chemical shifts are given as ö values in ppm; reference substances and signs for ö are shown in the scheme below: increasing field ~ ö=O for 1H + Si(CH3)4 11ß + BF3 · O(C2Hsl2 Coupling constants in Hz are given as "J (A, 8) 13C and + Si(CH3)4 refer to Labelied structural formulas, n is number of bonds between the coupled nuclei. 19f CFCL3 + 31p + H3P04 Multiplicities of the signals are abbreviated as s, d, t, q (singlet to quartet), quint, sext, sept, oct (quintet to octet), and m (multiplet); terms like dd (double doublet) and dq (double quartet) arealso used. Assignments referring to Labelied structural formulas are given in the form C-4, H-3,5. For Mössbauer spectra both the isomer shift ö and the quadrupole splitting ß are given in mm/s; the reference substances for ö are indicated after the numerical value, e.g. ö = 0.31 (57Co/Cu). Optical spectra are Labelied as IR (infrared) and UV (electronic spectrum including the visible region): IR bands are given in cm-1; the assigned bands are usually Labelied with the symbols v for Stretching vibration and ö and y for deformation Vibrations in-plane and out-of plane, respectively. The indices "s" and "a" mean symmetrical and asymmetrical. lntensities occur in parentheses in the common qualitative terms (s, m, w, vs, br., etc.). The UV absorption maxima, Amax• are given in nm followed bythe extinction coefficient e(L·cm-1· mol-1) orlogEin parentheses; sh means shoulder.