Table Of ContentHelmut Werner Gerhard Erker (Eds.)
Organometallics
in Organic Synthesis 2
Aspects of a Modern Interdisciplinary Field
Contributors:
F. Bickelhaupt, H. Brunner, A. de Meijere, R. Gleiter,
W.D. Jones, Th. Kauffmann, A. Nakamura, H.-U. ReiBig,
A. Salzer, K. Schlagl, H. Schwarz, G. Suss-Fink, H. tom Dieck,
H. Vahrenkamp, P. Vogel, G. Wilke, U. Zenneck
With 223 Figures and Schemes and 11 Tables
Springer-Verlag Berlin Heidelberg New York
London Paris Tokyo Hong Kong
Prof. Dr. Helmut Werner
Institut fur Anorganische Chemie der Universitat Wurzburg
Am Hubland, D-8700 Wurzburg
Prof. Dr. Gerhard Erker
Institut fur Organische Chemie der Universitat Wiirzburg
Am Rubland, D-8700 Wiirzburg
Proceedings of the Second Symposium on
"Organic Synthesis via Organometallics"
Wiirzburg/FRG,19.-22.1O.1988
Sponsored by the Stiftung Volkswagenwerk, Hannover, FRG
ISBN -13 :978-3-540-50531-0 e-ISBN -13 :978-3-642-74 269-9
DOl: 10.1007/978-3-642-74269-9
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Preface
Organometallic chemistry had its origins and its first period of
recognition in relation to organic synthesis in the last century.
Starting with the exciting work of Frankland and confirmed by the
even more impressive investigations of Grignard, organometallic
compounds became v1ell established being of considerable value to
the organic chemist. Later, the use of organolithium and
organoaluminium reagents, mainly developed by Wittig and Ziegler
in the middle of this century, received wide-spread attention.
The importance of organotransition-metal complexes as reagents or
catalysts in organic synthesis was a more recent discovery.
Following some pioneering work carried out in Europe, the United
States and Japan, various research groups throughout the world
have found new applications for the steadily growing number of
organometallic compounds, particularly of the transition metals.
To streamline these efforts, the "Volkswagen Stiftung", which from
the very beginning supported research in newly developing areas,
initiated in 1986 a new programme entitled "Organic Synthesis via
Organometallics". Already in its first year this has turned out to
be a great success. The enthusiasm and the continuing interest
among academic and industrial chemists led to a first symposium in
Hamburg in February 1987 which was found to be a great stimulus
for most of the participants. To retain this momentum, the
authorities of the "Volkswagen Stiftung" spontaneously agreed to
sponsor a second symposium which was held in Wlirzburg in October
1988. During three days, eighteen main lectures were presented by
VI
distinguished scientists from Germany and abroad covering various
aspects of this interdisciplinary field. Almost all of the
contributions are collected in this volume which hopefully will
stimulate new ideas and further cooperation between chemists from
different areas.
Our special thanks go to the authors for their willingness to
submit a manuscript and for their collaboration in this endeavor.
Wurzburg, 30. Marz 1989 Helmut Werner
Gerhard Erker
~ist of contributors
Prof. Dr. Friedrich Bickelhaupt, Scheikundig Laboratorium, Vri je
Universiteit Amsterdam, De Boelelaan 1083, NL-1081 HV Amsterdam
Prof. Dr. Henri Brunner, Insti tut fur Anorganische Chemie der
Universitat Regensburg, UniversitatsstraBe 31, 0-8400 Regensburg
Prof. Dr. Armin de Meijere, Institut fur Organische Chemie der
Universitat Hamburg, Martin-Luther-King-Platz 6, 0-2000 Hamburg 13
Prof. Dr. Rolf Gleit er, Organisch-Chemisches Insti tut der
Universitat Heidelberg, Im Neuenheimer Feld 270, 0-6900 Heidelberg·
Prof. Dr. William D. Jones, Department of Chemistry, University of
Rochester, River Station, Rochester, New York 14627, USA
Prof. Dr. Thomas Kauffmann, Organisch-Chemisches Institut,
Westfalische Wilhelms-Universitat Munster, CorrensstraBe 40, 0-
4400 Munster
Prof. Dr. Akira Nakamura, Department of Macromolecular Science,
Faculty of Science, Osaka University, Toyonaka, Osaka 560, Japan
Prof. Dr. Hans-Ulrich ReiBig, Institut fur Organische Chemie,
Technische Hochschule Darmstadt, PetersenstraBe 22, 0-6100
Darmstadt
Priv . Doz. Dr. Albrecht Salzer, Anorganisch-Chemisches Insti tut
der Universitat Zurich, WinterthurerstraBe 190, CH-8057 Zurich
Prof. Dr. Karl Schlagl, Institut fur Organische Chemie der
Universitat Wien, Wahringer StraBe 38, A-1090 Wien 9
Prof. Dr. Helmut Schwarz, Technische Universitat Berlin, Institut
fur Organische Chemie, StraBe des 17. Juni 135, 0-1000 Berlin 12
VIII
Prof. Dr. Georg Suss-Fink, Institut de Chimie, Universite de
Neuchatel, Avenue de Bellevaux 51, CH-2000 Neuchatel
Prof. Dr. Heindirk tom Dieck, Institut fur Anorganische und
Angewandte Chemie der Universitat Hamburg, Martin-Luther-King
Platz 6, 0-2000 Hamburg 13
Prof. Dr. Heinrich Vahrenkamp, Institut fur Anorganische und
Analytische Chemie, Albert-Ludwigs-Universitat Freiburg,
AlbertstraBe 21, 0-7800 Freiburg
Prof. Dr. Pierre Vogel, Insti tut de Chimie Organique, Univ ersi te
de Lausanne, Rue de la Barre 2, CH-1005 Lausanne
Prof. Dr. GUnther Wilke, Max-Planck-Institut fur Kohlenforschung,
Kaiser-Wilhelm-Platz 1, 0-4330 Mulheim a. d. Ruhr
Dr. Ulrich Zenneck, Anorganisch-Chemisches Institut der
Universitat Heidelberg, Im Neuenheimer Feld 270, 0-6900 Heidelberg
CON TEN T S
Page
G. Wilke
Organic Syntheses via Organometallics 1
H. tom Dieck*, C. Munz and J. Ehlers
Diazadiene-Controlled C-C Coupling Reactions on 21
Palladium and Iron
D. Hu, H. Pritzkow, H. Schaufele, C. Tolxdorff,
and U. Zenneck*
Highly Reactive x-Arene Iron Complexes and Their Use in 45
Stoichiometric and Catalytic Cyclic Addition Reactions
K. Schlogl
Stereochemistry of Arenetricarbonylchromium Complexes - 63
Useful Intermediates for Stereoselective Syntheses
P. vogel* and R. Roulet
Ironcarbonyl Complexes of Exocyclic Polyenes. The 79
Tricarbonyl(1,3-diene)iron Moiety as Remote Substituent
R. Gleiter*, M. Karcher, D. Kratz, S. Rittinger and
V. Schehlmann
Metal-Induced Dimerisations of Cyclic Diacetylenes 109
G. SUss-Fink
Novel Catalytic Applications of Ruthenium Clusters 127
A. Nakamura* and H. Yasuda
Selective Organic Synthesis by Diene Complexes of Early 137
Transition Metals
F. Bickelhaupt
Metallacyclobutanes: Synthons and Catalysts 145
x
Th. Kauffmann
New Properties of Reagents by Complexation of Carbanions 161
on Transition-Metals: Which Metal is in Each Case the
Most Favorable One?
W. D. Jones*, V. L. Chandler, R. P. Duttweiler, Jr.,
F. J. Feher, E. T. Hessell, G. C. Hsu and W. P. Kosar
Organometallic Transformations via C-H Bond Activation 185
G. Czekay, T. Drewello, K. Eller, C. B. Lebrilla, T. Prusse,
C. Schulze, N. Steinruck, D. Sulzle, T. Weiske and H. Schwarz*
Remote Functionalization of Carbon-Hydrogen and Carbon- 203
Carbon Bonds by Bare Transition Metal Ions in the Gas
Phase
H. Vahrenkamp
Aktivierung von Mehrfachbindungssystemen auf Clustern 235
A. de Meijere*, A. Kaufmann, R. Lackmann, H.-C. Militzer,
O. Reiser, S. Schomenauer and A. Weier
Directed - and Undirected - Syntheses of Novel Organic 255
Compounds via Iron, Cobalt and Chromium Complexes
H. Brunner
Enantioselective Synthesis of Organic Compounds with 277
Optically Active Transition Metal Catalysts and Transition
Metal Compounds
A. Salzer
Diolefin Iron Complexes - Useful and Versatile Tools in 291
Organic Synthesis
R. U. ReiBig
Donor-Acceptor-Substituted Cyclopropanes via Fischer 311
Carbene Complexes
ORGANIC SYNTHESES VIA ORGANOMETALLICS
G. Wilke
Max-Planck-Instiut fUr Kohlenforschung
Kaiser-Wilhelm-Platz 1. 4330 Mulheim an der Ruhr. FRG
In 1890 Mond. Lange and Quinkel) discovered the synthesis of Ni(CO)4 from
metallic nickel and carbon monoxide. A few years later Sabatier and
Senderens2) were led to attempt the preparation of a volatile compound similar to
Ni[COI4 using ethene instead of carbon monoxide. but without success.
Nevertheless, in the course of these experiments they discovered catalytic
hydrogenation. More than 60 years later we were able to realize the original idea
of Sabatier in part when we managed to prepare first Ni[CODI/) and later
Ni[C2H4134). Numerous complexes of nickel(O) have since been synthesized.
Today I would like to describe the application of nickel complexes in stoichiometric
as well as in catalytic reactions. Cyclooligomerizations of unsaturated substrates
mediated by nickel(O) are characterized by the very general phenomena of oxidative
addition and reductive elimination. The following example represents these types
of reactionS).
j-
coo
- 85'/.
H. Werner and G. Erker (Eds.)
Organometallics in Organic Synthesis 2
© Springer-Verlag Berlin Heidelberg 1989
