Ge Organogermanium Compounds: Part 2: Ge(CH3)3R and Ge(C2H5)3R Compounds

406 Pages·1988·7.954 MB·English

by  Frank Glockling (auth.), Ulrich Krüerke, Wolfgang Petz, Christa Siebert (eds.)

GmeLin Handbook of Inorganic Chemistry
8th Edition
Gmelin Handbook
of Inorganic Chemistry
8th Edition
GmeLin Handbuch der Anorganischen Chemie
Achte, v6lLig neu bearbeitete Auflage
Prepared GmeLin-lnstitut fOr Anorganische Chemie
and issued by der Max-Planck-Gesellschaft
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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 1989
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der Max-Planck-Gesellschaft zur Forderung der Wissenschaften
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Universitat Marburg), Prof. Dr. N. N. Greenwood (University of Leeds), Prof. Dr. H. Grunewald
(Bayer AG, Leverkusen), Prof. Dr. H. Harnisch (Hoechst AG, Frankfurt/Main-Hochst), Prof. Dr.
H. Noth (Universitat Munchen), Prof. Dr. H. Offermanns (Degussa AG, Frankfurt/Main), Prof.
Dr. G. zu Putlitz (Universitat Heidelberg), Prof. Dr. A. Rabenau (Max-Planck-Institut fur Fest
korperforschung, Stuttgart), Prof. Dr. A. Simon (Max-Planck-Institut fUr Festkorperforschung,
Stuttgart), Prof. Dr. Dr. A. H. Staab (Prasident der Max-Planck-Gesellschaft, Munchen), Prof.
Dr. Dr. h.c. mUlt. G. Wilke (Max-Planck-Institut fUr Kohlenforschung, Mulheim/Ruhr)
DIRECTOR DEPUTY DIRECTOR
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CORRESPONDENT MEMBERS OF THE SCIENTIFIC STAFF Dr. B. Baker, Dr. P. L. Bayless,
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CORRESPONDENT MEMBERS OF THE INSTITUTE Prof. Dr. Hans Bock
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STAFF GMELIN HANDBOOK
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Koeppel, Dipl.-Chem. H. Kottelwesch, R. Kolb, E. Kranz, Dipl.-Chem. I. Kreuzbichler, Dr. A.
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Petz, I. Rangnow, Dr. B. Rempfer, Dipl.-Phys. H.-J. Richter-Ditten, Dipl.-Chem. H. Rieger, E.
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K. Schucke, A. Schwarzel, Dr. B. Schwager, Dipl.-Ing. H. M. Somer, G. Strauss, Dr. G. Swoboda,
Dr. U. Taubald, M. Teichmann, Dr. D. Tille, Dipl.-Ing. H. Vanecek, Dipl.-Chem. P. Velie, Dipl.
Ing. U. Vetter, H.-M. Wagner, Dipl.-Phys. J. Wagner, R. Wagner, Dr. E. Warkentin, Dr. C. Weber,
Dr. A. Wietelmann, Dr. M. Winter, Dr. B. Wobke, K. Wolff
STAFF GMELIN ONLINE DATA SYSTEM
Dr. R. Deplanque, Dr. P. Kuhn, Dr. G. Olbrich
Organometallic 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)
Be Organoberyllium Compounds 1 (1987)
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 Organocopper Compounds 1 (1985), 2 (1983), 3 (1986), 4 (1987), Index (1987)
Fe Eisen-Organische Verbindungen A 1 (1974), A 2 (1977), A 3 (1978), A 4 (1980), A 5
(1981), A6 (1977), A 7 (1980), A8 (1985), B 1 (partly in English; 1976), Organoiron
Compounds B 2 (1978), Eisen-Organische Verbindungen 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), B 13 (1988), B 14 (1989), B 15 (1989), Eisen-Organische
Verbindungen C 1 (1979), C 2 (1979), Organoiron Compounds C 3 (1980), C 4 (1981),
C5 (1981), C7 (1985), and Eisen B (1929-1932)
Ga Organogallium Compounds 1 (1986)
Ge Organogermanium Compounds 1 (1988),2 (1989) present volume
Hf Organohafnium 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)
Pb Organolead Compounds 1 (1987)
Pt Platin C (1939) and 0 (1957)
Re Organorhenium 1 (1989)
Ru Ruthenium Erg.-Bd. (1970)
Sb Organoantimony Compounds 1 (1981),2 (1981), 3 (1982), 4 (1986)
Sc, Y, 06(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), 13
(1986), 14 (1987), 15 (1988), 16 (1988)
Ta Tantal B 2 (1971)
Ti Titan-Organische Verbindungen 1 (1977), 2 (1980), Organotitanium Compounds 3
(1984), 4 and Register (1984)
U Uranium Suppl. Vol. E 2 (1980)
V Vanadium-Organische Verbindungen (1971), Vanadium B (1967)
Zr Organozirconium Compounds (1973)
Gmelin Handbook
of Inorganic Chemistry
8th Edition
Ge
Organogermanium
Compounds
Part 2
Ge(CH3bR and
Ge(C2HSbR Compounds
With 3 illustrations
AUTHOR Frank Glockling
University of Oxford
FORMULA INDEX Bernd Kalbskopf, Uwe Nohl,
Hans-JOrgen Richter-Ditten
EDITORS Ulrich KrOerke, Wolfgang Petz, Christa Siebert (Maintal)
CHIEF EDITOR Ulrich KrOerke
Springer-Verlag Berlin Heidelberg GmbH 1989
LITERATURE CLOSING DATE: 1985
Library of Congress Catalog Card Number: Agr 25-1383
ISBN 978-3-662-07390-2 ISBN 978-3-662-07388-9 (eBook)
DOI 10.1007/978-3-662-07388-9
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© by Springer-Verlag Berlin Heidelberg 1988
Originally published by Springer-Verlag Berlin Heidelberg New York London Paris Tokyo in 1989
Softcover reprint of the hardcover 8th edition 1988
The use of registered names, trademarks, etc., in this publication does not imply, even in the absence of a specific statement, that
such names are exempt from the relevant protective laws and regulations and therefore free for generaL use.
Preface
The present second voLume in the organogermanium series continues the description of
Ge(CH3bR compounds (Section 1.1.2.1), beginning with R = aLkenyL (Section 1.1.2.1.7, p.1)
and concLuding with R = heterocycLe (Section 1.1.2.1.12, p.93). The remaining part of the
voLume covers compLeteLy the type Ge(C2HSbR (Section 1.1.2.2), which is the most voLuminous
of the GeR3R compounds.
The arrangement of the organogermanium compounds within this series has been present
ed in the preface for VoLume 1. However, it may be usefuL to repeat the following expLanations
concerning the Location of compounds according to the type of the R' Ligand:
The term "substituted aLkyL" stands for aLkyL Ligands containing noncarbon atoms but aLso
incLudes aLkyL Ligands substituted by cycLoaLkyL, aryL, and heterocyclic groups, for exampLe,
CH2C6Hs and CH2CH2CH2CSHg-cycLo, which are arranged as substituted methyL and substituted
propyL, respectiveLy. In generaL, the Longest carbon chain beginning from the Ge atom deter
mines the Location of a compound and is illustrated as foLLows:
(a) Ge(CH3bCH2CH(OH)CH(CH3)CH3 derivative of Ge(CH3bC4Hg-n
(b) Ge(CH3bCH(C6Hs)CH200CCH3 derivative of Ge(CH3bC2HS
(c) Ge(C2HsbCF2COCF3 derivative of Ge(C2HsbC3Hrn
(d) Ge(C6HsbCH2CH(OCH2CH=CH2)CH3 derivative of Ge(C6HsbC3Hrn
ExampLes (b) and (d) show that a group beyond a heteroatom (e.g., aLLyL on oxygen) does not
count for the generaL Location of a compound. Common branched hydrocarbon groups Like
i-C3H7 or t-C4Hg are specifically identified.
These ruLes naturally aLso appLy to compounds with aLkenyL and aLkynyL Ligands. In generaL,
the arrangement is handLed somewhat flexibLy and is adapted to the scope and kind of materiaL
to be described. AdditionaL expLanations are frequentLy given at the beginning of a section.
As a ruLe the nomencLature recommended by IUPAC has been foLLowed. But compound
names are LargeLy avoided since many of the compounds are onLy presented in tabLes and
identified by their formuLas. Much of their data in the tabLes occurs in abbreviated form without
units; generaL expLanations are given on p. X.
The voLume concLudes with an empiricaL formuLa index (p. 297) and a Ligand formuLa index
(p.329).
Frankfurt am Main ULrich KrOerke
November 1988
x
Explanations, Abbreviations, and Units
Most compounds in this volume are presented in tables in which numerous abbreviations
are used and the units are omitted for the sake of brevity. This necessitates the following
clarification.
The formation of a compound is briefly described at the first place in the third column of a
table. Evident procedures of a preparation such as hydrolysis after an organometallic reaction,
evaporation of solvent, drying, etc., are usually omitted; 20°C replaces frequently the term
"room temperature" in the origina!. GLC or TLC stand for gas-liquid or thin-layer
chromatography.
Abbreviations for solvents and other substances are as follows: AIBN for azobisisobutyro
nitrile, DMF for dimethylformamide, DMSO for dimethyl sulfoxide, HMPT for hexamethylphos
phoric triamide, THF for tetrahydrofuran, TMEDA for tetramethylethylenediamine.
Temperatures are given in °C, 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. Terms like 80°/0.1 mean the bOiling or sUblimation point at a pressure
of 0.1 Torr. Densities are given in g/cm3; dt is the density at t °C referred to water at 4°C.
NMR represents nuclear magnetic resonance. Chemical shifts are given as 8 values in ppm
and positive to low field from the following reference substances: Si(CH3)4 for 1H and 13C,
CFC13 for 19F, H3P04 for 31p, and Ge(CH3)4 for 73Ge. Multiplicities of the signals are abbreviated
as s, d, t, q (singlet to quartet), quint, sext, sept (quintet to septet), and m (multiplet); terms
like dd (double doublet) and t's (triplets) are also used. Assignments referring to labeled
structural formulas are given in the form C-4, H-3,S. Carbon and hydrogen atoms are labeled
1, 2, 3 ... n beginning with the Ge-bonded carbon atom. Coupling constants J in Hz appear
usually in parentheses behind the 8 value, along with the multiplicity and the assignment, and
refer to the respective nucleus. If a more precise designation is necessary, they are given as,
e.g., nJ(C, H) or J(1, 3) referring to labeled formulas.
Nuclear quadrupole resonance is abbreviated NOR, with the transitions in MHz.
Optical spectra are labeled as IR (infrared), R (Raman), and UV (electronic spectrum
including the visible region). IR bands and Raman lines are given in cm-1; the assigned
bands are usually labeled with the symbols v for stretching vibration and 8 for deformation
vibration. Intensities occur in parentheses either in the common qualitative terms (s, m, w,
vs, etc.) or as numerical relative intensities. The UV absorption maxima, Amax, are given in
nm followed by the extinction coefficient E (L . cm -1 . mol-1) or log E in parentheses; sh means
shoulder.
Photoelectron spectra are abbreviated PE, e.g., PE/He(I), with the ionization energies
in eV.
Hyperfine couplings of ESR spectra are given as a(N) in Gauss where N designates the
respective nucleus.
Solvents or the physical state of the sample and the temperature (in °C or K) are given in
parentheses immediately after the spectral symbol, e.g., R (solid), 13C NMR (C6D6, SO°C), or
at the end of the data if spectra for various media are reported. Common solvents are given
by their formulas (C6H12 = cyclohexane) or abbreviations explained above.
The fragments of mass spectra, abbreviated MS, are given in brackets followed by the
relative intensity in parentheses; [M]+ is the molecular ion.
XI
Table of Contents
Page
1.1.2 Tetraorganogermanium Compounds of the GeR3R' Type
1.1.2.1 Ge(CH3hR Compounds . ....
Ge(CH3hR Compounds with R = ALkenyL .
Ge(CH3hR Compounds with R = Cyclic and PoLycyclic ALkenyL . 28
Ge(CH3hR Compounds with R = ALkynyL . 51
Ge(CH3hR Compounds with R = AryL . . 68
Ge(CH3hR Compounds with R = Heterocyclic Group 93
1.1.2.2 Ge(C2HShR Compounds . . . 110
Ge(C2HshR Compounds with R = ALkyL 110
Ge(C2HShR Compounds with R = Substituted ALkyL 115
Ge(C2HshR Compounds with R = Substituted MethyL 115
Ge(C2HShR Compounds with R = Substituted EthyL . 124
Ge(C2HShR Compounds with R = Substituted PropyL 143
Ge(C2HshR Compounds with R = Substituted ALkyL Larger than PropyL 158
Ge(C2HshR Compounds with R = CycLoaLkyL and Substituted CycLoaLkyL . 167
Ge(C2HShR Compounds with R = ALkenyL . . . . . 169
Ge(C2HShR Compounds with R = Substituted ALkenyL 187
Ge(C2HshR Compounds with R = C2 ALkenyL 187
Ge(C2HShR Compounds with R = C3 ALkenyL . . . 203
Ge(C2HshR Compounds with R = C4 ALkenyL . . . 211
Ge(C2HShR Compounds with R = Cn ALkenyL where n > 4 221
Ge(C2HShR Compounds with R = Cyclic and PoLycyclic ALkenyL 229
Ge(C2HShR Compounds with R = ALkynyL . . . . . 236
Ge(C2HshR Compounds with R = Substituted ALkynyL 251
Ge(C2HshR Compounds with R = C2 ALkynyL . . . 251
Ge(C2HshR Compounds with R = Cn ALkynyL where n > 2 259
Ge(C2HSbR Compounds with R = Aromatic Group . 274
Ge(C2HSbR Compounds with R = Heterocyclic Group 285
Empirical Formula Index . 297
Ligand Formula Index . . 329
Physical Constants and Conversion Factors 397