Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Notes
- 1.
In English: “Perception means bringing together observations and the inner ideas, and reconciling their agreement”.
- 2.
Interestingly, more recent MO calculations on silver(I) and copper(I) complexes have indicated that there is much less back donation between these metals and the olefin than in the related platinum compounds, and that the interaction might be primarily electrostatic (see [32], p. 4).
- 3.
In his textbook “Organotransition Metal Chemistry” (Wiley Interscience, New York, 1986) Akio Yamamoto included several short paragraphs entitled “Intermezzos”, in which he mentioned some anecdotes presented during his classes at the Tokyo Institute of Technology “to help students stay awake”. In one of those intermezzos, Akio reported that in the course of his lectures Wilke frequently called the catalytically active nickel complexes having no supporting ligands such as CO, PR3 or cyclopentadienyl “naked nickel”. An American chemist thus nicknamed him “a man who brought sex into chemistry” and it seems that Wilke enjoyed this name.
- 4.
In one of his essays [113], Wolfgang Herrmann (see Fig. 9.4) referred the reader to a paper by Paul Sabatier (Nobel laureate for Chemistry 1912), in which he mentioned that he attempted to coordinate molecules such as N2O, NO, NO2, ethene, acetylene, etc. to nickel in a similar way as it was done by Mond for the preparation of nickel tetracarbonyl. Sabatier observed that “when ethylene was passed through a column containing nickel, no reaction occurs at ordinary temperature....but above 300°C the column starts to glow and the gas begins to decompose; not only carbon and hydrogen are produced, but also larger amounts of ethane. The latter compound must have come from hydrogenation of ethylene resulting from some special property of nickel, which appeared to be a hydrogenation catalyst”. Though no olefin nickel complex was formed (possibly as a short-lived intermediate), this observation initiated a series of further investigations which finally led to the Nobel prize.
- 5.
see [69], p. 102.
- 6.
[69], Editor’s Note, p. xix.
References
P. Pfeiffer, Organische Molekülverbindungen (Verlag Ferdinand Enke, Stuttgart, 1927, p. 209).
M. S. Kharasch, and T. A. Ashford, Coordination Compounds of Platinous Halides with Unsaturated (Ethylene) Substances, J. Am. Chem. Soc. 58, 1733–1738 (1936).
R. N. Keller, Coordination Compounds of Olefins with Metallic Salts, Chem. Rev. 28, 229–267 (1941).
W. C. Zeise, Ueber Acechlorplatin, nebst Bemerkungen über einige andere Producte der Einwirkung zwischen Platinchlorid und Aceton, J. Prakt. Chem. 20, 193–234 (1840).
W. Prandtl, and K. A. Hofmann, Ueber Platin-Kohlenstoff-Verbindungen, Ber. dtsch. chem. Ges. 33, 2981–2983 (1900).
R. D. Gillard, B. T. Heaton, and M. F. Pilbrow, 4-Methylpent-4-en-2-one (Isomesityl Oxide) Complex of Platinum(II), J. Chem. Soc. A 1970, 353–355.
C. Liebermann, and C. Paal, Ueber Derivate des Allylamins, Ber. dtsch. chem. Ges. 16, 523–534 (1883).
M. Herberhold, Metal π-Complexes, Vol. II: Complexes with Mono-Olefinic Ligands (Elsevier, Amsterdam, 1972, Chapter 2).
R. G. Denning, and L. M. Venanzi, Platinum Complexes with Unsaturated Amines. Part I. Complexes with Allylamines, J. Chem. Soc.3241–3247 (1963).
E. Biilmann, Ueber die Einwirkung von Allylalkohol auf Kaliumplatochlorid, Ber. dtsch. chem. Ges. 33, 2196–2201 (1900).
P. Pfeiffer, and H. Hoyer, Komplexverbindungen der Äthylenkörper mit Platinsalzen, Z. anorg. allg. Chem. 211, 241–248 (1933).
K. A. Hofmann, and J. von Narbutt, Verbindungen von Platinchlorür mit Di-cyclopentadien, Ber. dtsch. chem. Ges. 41, 1625–1628 (1908).
J. R. Doyle, and H. B. Jonassen, The Structure of Dicyclopentadienedichloroplatinum(II), J. Am. Chem. Soc. 78, 3965–3967 (1956).
N. C. Baenziger, J. R. Doyle, G. F. Richards, and L. C. Carpenter, Advances in the Chemistry of the Coordination Compounds (McMillan, New York, 1961, p. 136).
A. D. Hel’man, Complex Compounds of Platinum and Butadiene (Bivinyl), Dokl. Akad. Nauk SSSR 23, 532–536 (1939).
A. D. Hel’man, Reaction of Unsaturated Molecules with Sodium Chloroplatinate, Dokl. Akad. Nauk SSSR 31, 761–764 (1941).
P. E. Slade Jr., and H. B. Jonassen, Coordination Compounds of Butadiene with Platinum(II), Palladium(II) and Copper(I) Halides, J. Am. Chem. Soc. 79, 1277–1279 (1957).
M. S. Kharasch, R. C. Seyler, and F. R. Mayo, Coordination Compounds of Palladous Chloride, J. Am. Chem. Soc. 60, 882–884 (1938).
J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, R. Rüttinger, and H. Kojer, Katalytische Umsetzungen von Olefinen an Platinmetall-Verbindungen, Angew. Chem. 71, 176–182 (1959).
L. Hintermann, Wacker Type Oxidations, in. Transition Metals for Organic Synthesis, Second Ed. (Eds. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 2004, Vol. 2, Chapter 2.8).
M. Berthelot, Observations relatives à l’action des sels cuivreux sur les carbures d’hydrogène et sur l’oxyde de carbone, Ann. Chim. Phys. 23, 32–39 (1901).
W. Manchot, and W. Brandt, Ueber die Cuproverbindungen des Aethylens und des Kohlenoxyds, Liebigs Ann. Chem. 370, 286–296 (1909).
H. Tropsch, and W. J. Mattox, Absorption of Ethylene by Solid Cuprous Chloride, J. Am. Chem. Soc. 57, 1102–1103 (1935).
E. R. Gilliland, J. E. Seebold, J. R. FitzHugh and P. S. Morgan, Reaction of Olefins with Solid Cuprous Halides, J. Am. Chem. Soc. 61, 1960–1962 (1939).
W. F. Eberz, H. J. Welge, D. M. Yost, and H. J. Lucas, The Rate of Hydration of Isobutene in the Presence of Silver Ion. The Nature of the Isobutene–Silver Complex, J. Am. Chem. Soc. 59, 45–49 (1937).
S. Winstein, and H. J. Lucas, The Coordination of Silver Ion with Unsaturated Compounds, J. Am. Chem. Soc. 60, 836–847 (1938).
K. S. Pitzer, Electron Deficient Molecules. I. The Principle of Hydroboron Structures, J. Am. Chem. Soc. 67, 1126–1132 (1945).
H. Reihlen, A. Gruhl, G. von Hessling, and O. Pfrengle, Über Carbonyle und Nitrosyle, Liebigs Ann. Chem. 482, 161–182 (1930).
E. Krause and A. von Grosse, Die Chemie der metall-organischen Verbindungen (Gebrüder Bornträger, Berlin, 1937).
H. J. Emeléus, and J. S. Anderson, Modern Aspects of Inorganic Chemistry (Routledge and Kegan Paul Ltd., London, 1952, Chapter 8).
M. J. S. Dewar, A Review of the π-Complex Theory, Bull. Soc. Chim. Fr. 1951, C71–C79 (1951).
D. P. M. Mingos, A Historical Perspective on Dewar’s Landmark Contribution to Organometallic Chemistry, J. Organomet. Chem. 635, 1–8 (2001).
M. J. S. Dewar, Mechanism of the Benzidine and Related Rearrangements, Nature 156, 784 (1945).
M. J. S. Dewar, The Mechanism of Benzidine-type Rearrangements, and the Role of π-Electrons in Organic Chemistry, J. Chem. Soc. 1946, 406–408.
A. D. Walsh, Structures of Ethylene Oxide and Cyclopropane, Nature 159, 165 (1947).
H. J. Taufen, M. J. Murray, and F. F. Cleveland, Effect of Silver Ion Coordination Upon the Raman Spectra of Some Unsaturated Compounds, J. Am. Chem. Soc. 63, 3500–3503 (1941).
J. Chatt, The Addition Compounds of Olefins with Mercuric Salts, Chem. Rev. 48, 7–43 (1951).
J. Chatt, and L. A. Duncanson, Infrared Spectra and Structure: Attempted Preparation of Acetylene Complexes, J. Chem. Soc. 1953, 2939–2947.
M. J. S. Dewar, and G. P. Ford, Relationship Between Olefinic π Complexes and Three-Membered Rings, J. Am. Chem. Soc. 101, 783–791 (1979).
G. J. Kubas, Metal–Dihydrogen and σ-Bond Coordination: The Consummate Extension of the Dewar-Chatt-Duncanson Model for Metal–Olefin π Bonding, J. Organomet. Chem. 635, 37–68 (2001).
J. Chatt, L. M. Vallarino, and L. M. Venanzi, Diene Complexes of Platinum(II). The Structure of Hofmann and von Narbutt’s [Dicyclopentadiene(RO)PtCl], J. Chem. Soc. 1957, 2496–2505.
J. Chatt, L. M. Vallarino, and L. M. Venanzi, Some Diene Complexes of Palladium(II) and Their Alkoxy Derivatives, J. Chem. Soc. 1957, 3413–3416.
J. Chatt, and L. M. Venanzi, Diene Complexes of Rhodium(I), J. Chem. Soc. 1957, 4735–4741.
E. W. Abel, M. A. Bennett, and G. Wilkinson, Norbornadiene-Metal Complexes and Some Related Compounds, J. Chem. Soc. 1959, 3178–3182.
R. Cramer, μ-Dichlorotetraethylenedirhodium(I), Inorg. Chem. 1, 722–723 (1962).
L. Porri, A. Lionetti, G. Allegra, and A. Immirzi, Dibutadienerhodium(I) Chloride, Chem. Comm. 1965, 336–337.
G. Winkhaus, and H. Singer, Rhodium(I)-Komplexe mit Mono- und Diolefinen, Chem. Ber. 99, 3602–3609 (1966).
R. R. Schrock, and J. A. Osborn, Catalytic Hydrogenation Using Cationic Rhodium Complexes. I. Evolution of the Catalytic System and the Hydrogenation of Olefins, J. Am. Chem. Soc. 98, 2134–2143 (1976).
H. Werner, M. E. Schneider, M. Bosch, J. Wolf, J. H. Teuben, A. Meetsma, and S. I. Troyanov, Cationic and Neutral Diphenyldiazomethanerhodium(I) Complexes as Catalytically Active Species in the CC Coupling Reaction of Olefins with Diphenyldiazomethane, Chem. Eur. J. 6, 3052–3059 (2000).
B. Rybtchinski, S. Oevers, M. Montag, A. Vigalok, H. Rozenberg, J. M. L. Martin, and D. Milstein, Comparison of Steric and Electronic Requirements for CC and CH Bond Activation. Chelating vs. Nonchelating Case, J. Am. Chem. Soc. 123, 9064–9077 (2001).
B. F. Hallam, and P. L. Pauson, Butadiene- and cycloHexadiene-iron Tricarbonyls, J. Chem. Soc. 1958, 642–645.
O. S. Mills, and G. Robinson, The Structure of Butadieneiron Tricarbonyl, Proc. Chem. Soc. 1960, 421–422.
R. Burton, M. L. H. Green, E. W. Abel, and G. Wilkinson, Some New Organo-iron Complexes, Chem. & Ind. 1958, 1592.
R. Pettit, Metal Complexes with 2,2,1-Bicycloheptadiene, J. Am. Chem. Soc. 81, 1266 (1959).
T. A. Manuel, and F. G. A. Stone, Cyclooctatetraene-Iron Complexes, Proc. Chem. Soc. 1959, 90.
A. Nakamura, and N. Hagihara, Cyclooctatetraeneiron Tricarbonyl, Bull. Chem. Soc. Jpn. 32, 880–881 (1959).
M. D. Rausch, and G. N. Schrauzer, Cyclooctatetraeneiron Tricarbonyl and Cyclooctatetraenediiron Hexacarbonyl, Chem. & Ind. 1959, 957–958.
E. W. Abel, M. A. Bennett, and G. Wilkinson, Cycloheptatriene Metal Complexes, Proc. Chem. Soc. 1958, 152–153.
E. W. Abel, M. A. Bennett, R. Burton, and G. Wilkinson, The cycloHeptatriene-Metal Complexes and Related Compounds, J. Chem. Soc. 1958, 4559–4563.
M. A. Bennett, L. Pratt, and G. Wilkinson, Proton Resonance Spectra of Cycloheptatriene Complexes of Group VI Metals, J. Chem. Soc. 1961, 2037–2044.
T. A. Manuel, and F. G. A. Stone, 1,5-Cyclooctadienetungstentetracarbonyl, Chem. & Ind. 1959, 1349–1350.
M. A. Bennett, and G. Wilkinson, Some New Olefin Complexes of Mo(0) and Ru(II), Chem. & Ind. 1959, 1516.
E. O. Fischer, and W. Fröhlich, Zur Komplexbildung des Cyclooctadiens-(1.5) mit Metallhexacarbonylen, Chem. Ber. 92, 2995–2998 (1959).
B. Dickens, and W. N. Lipscomb, Molecular and Valence Structures of Complexes of Cyclooctatetraene with Iron Carbonyl, J. Chem. Phys. 37, 2084–2093 (1962).
J. D. Dunitz, and P. Pauling, Struktur des Cycloheptatrien-molybdän-tricarbonyls, C7H8Mo(CO)3, Helv. Chim. Acta 43, 2188–2197 (1960).
T. A. Manuel, and F. G. A. Stone, Cyclooctatetraene Iron Tricarbonyl and Related Compounds, J. Am. Chem. Soc. 82, 366–372 (1960).
E. O. Fischer, and H. Werner, Metal π-Complexes, (Elsevier, Amsterdam, 1966, Vol. I, p. 127).
F. A. Cotton, Bonding of Cyclooctatetraene to Metal Atoms: Simple Theoretical Considerations, J. Chem. Soc. 1960, 400–406.
F. G. A. Stone, Leaving No Stone Unturned (American Chemical Society, Washington, DC, 1993, p. 36).
F. A. Cotton, Fluxional Organometallic Molecules, Acc. Chem. Res. 1, 257–265 (1968).
H. Alper, Organic Syntheses with Iron Pentacarbonyl, in: Organic Synthesis via Metal Carbonyls (Eds. I. Wender and P. Pino, Wiley Interscience, New York, 1977, Vol. 2, pp. 545–593).
A. J. Pearson, Metallo-organic Chemistry (Wiley Interscience, New York, 1985, Chapters 7 and 8).
H. J. Dauben Jr., and L. R. Honnen, π-Tropenium-molybdenum-tricarbonyl Tetrafluoroborate, J. Am. Chem. Soc. 80, 5570–5571 (1958).
J. D. Munro, and P. L. Pauson, Reactions of Tricarbonyltropyliumchromium Perchlorate with Anions: A Novel Rearrangement, Proc. Chem. Soc. 1959, 267.
J. D. Munro, and P. L. Pauson, Cycloheptatriene- and Tropylium-Metal Complexes. Part I. The “Normal” Reaction of Tricarbonyltropyliumchromium Salts with Anions, J. Chem. Soc. 1961, 3475–3486.
A. Salzer, and H. Werner, Elektrophile und nucleophile Additionsreaktionen an Siebenringliganden in Tricarbonylmolybdän-Komplexen: Synthese von [C7H9Mo(CO)3]BF4, C7H9Mo(CO)3Cl und [C7H9P(C6H5)3]BF4, J. Organomet. Chem. 87, 101–108 (1975).
H. D. Murdoch, and E. Weiss, Eisencarbonylkomplexe des Äthylens und Hexatriens, Helv. Chim. Acta 46, 1588–1594 (1963).
E. Koerner von Gustorf, M. C. Henry, and C. Di Pietro, Photochemische Umsetzung von Fe(CO)5 mit Vinylchlorid, Styrol, Propylen und Vinyläthyläther, Z. Naturforsch., Part B, 21, 42–45 (1966).
H. P. Kögler, and E. O. Fischer, Cyclopentadienyl-mangan-äthylen-dicarbonyl, Z. Naturforsch., Part B, 15, 676 (1960).
E. O. Fischer, and M. Herberhold, Photochemische Substitutionsreaktionen an Cyclopentadienyl-mangan-tricarbonyl, in: Essays in Coordination Chemistry, Exper. Suppl. IX (Birkhäuser Verlag, Basel, 1964, p. 259–305).
E. O. Fischer, and P. Kuzel, Mesitylen-chrom(0)-äthylen-dicarbonyl, Z. Naturforsch., Part B, 16, 475–476 (1961).
J. A. Banister, S. M. Howdle, and M. Poliakoff, Preparative-scale Organometallic Chemistry in Supercritical Fluids; Isolation of [Cr(CO)5(C2H4)] as a Stable Solid at Room Temperature, J. Chem. Soc., Chem. Comm. 1993, 1814–1815.
I. W. Stolz, G. R. Dobson, and R. K. Sheline, Acetylene and Olefin Derivatives of Group VI Metal Carbonyls, Inorg. Chem. 2, 1264–1267 (1963).
E. Koerner von Gustorf, and F.-W. Grevels, Photochemistry of Metal Carbonyls, Metallocenes, and Olefin Complexes, Fortschr. Chem. Forsch. 13, 366–450 (1969).
F.-W. Grevels, J. Jacke, and S. Özkar, Photoreactions of Group 6 Metal Carbonyls with Ethene: Synthesis of trans-(η2-Ethene)2M(CO)4 (M = Cr, Mo, W), J. Am. Chem. Soc. 109, 7536–7537 (1987).
E. O. Fischer, H. P. Kögler, and P. Kuzel, Über neue π-Komplexe des Butadiens mit einfachen und substituierten Metallcarbonylresten, Chem. Ber. 93, 3006–3013 (1960).
M. Herberhold, Ph.D. Thesis, Universität München, 1963.
G. N. Schrauzer, Bisacrylonitrile Nickel and Related Complexes from the Reaction of Nickel Tetracarbonyl with Compounds Containing Activated Double Bonds, J. Am. Chem. Soc. 81, 5310–5312 (1959).
G. N. Schrauzer, Zur Kenntnis von Bis-acrylnitril-nickel(0), Chem. Ber. 94, 642–650 (1961).
G. N. Schrauzer, Some Advances in the Organometallic Chemistry of Nickel, Adv. Organomet. Chem. 2, 1–48 (1964).
G. N. Schrauzer, and H. Thyret, Zur Kenntnis von Bis-durochinon-nickel(0) and Cyclooctatetraene-durochinon-nickel(0), Z. Naturforsch., Part B, 16, 353–356 (1961).
G. N. Schrauzer, and H. Thyret, Neuartige ”Sandwich“-Verbindungen des Nickel(0). Zur Kenntnis von Durochinon-Nickel(0)-Komplexen mit cyclischen Dienen, Z. Naturforsch., Part B, 17, 73–76 (1962).
M. D. Glick, and L. F. Dahl, Structure and Bonding in 1,5-Cyclooctadiene-duroquinone-nickel, J. Organomet. Chem. 3, 200–221 (1965).
G. Wilke, Synthesen in der Cyclododekan-Reihe, Angew. Chem. 69, 397–398 (1957).
G. Wilke, Cyclooligomerization of Butadiene and Transition Metal π-Complexes, Angew. Chem. Int. Ed. Engl. 2, 105–115 (1963).
K. Fischer, K. Jonas, P. Misbach, R. Stabba, and G. Wilke, The “Nickel Effect”, Angew. Chem. Int. Ed. Engl. 12, 943–953 (1973).
H. W. B. Reed, The Catalytic Cyclic Polymerisation of Butadiene, J. Chem. Soc. 1954, 1931–1941.
G. Wilke, Neues über cyclische Butadien-Oligomere, Angew. Chem. 72, 581–582 (1960).
B. Bogdanovic, M. Kröner, and G. Wilke, Olefin-Komplexe des Nickel(0), Liebigs Ann. Chem. 699, 1–23 (1966).
D. J. Brauer, and C. Krüger, The Three-dimensional Structure of trans,trans,trans-1,5,9-Cyclododecatrienenickel, J. Organomet. Chem. 44, 397–402 (1972).
N. Rösch, and R. Hoffmann, Geometry of Transition Metal Complexes with Ethylene or Allyl Groups as the Only Ligands, Inorg. Chem. 13, 2656–2666 (1974).
K. Jonas, P. Heimbach, and G. Wilke, 1,5,9-Cyclododecatriene Complexes of Nickel, Angew. Chem. Int. Ed. Engl. 7, 949–950 (1968).
G. Wilke, Contributions to Organo-Nickel Chemistry, Angew. Chem. Int. Ed. Engl. 27, 185–206 (1988).
P. S. Skell, J. J. Havel, D. L. Williams-Smith, and M. J. McGlinchey, Reactions of Nickel Atoms with Unsaturated Hydrocarbons, J. Chem. Soc., Chem. Comm. 1972, 1098–1099.
P. W. Jolly, and G. Wilke, The Organic Chemistry of Nickel, Organonickel Complexes (Academic Press, New York, 1974, Vol. I, p. 258).
D. J. Brauer, and C. Krüger, The Stereochemistry of Transition Metal Cyclooctatetraenyl Complexes: Di-h3,h3’-cyclooctatetraenedinickel, a Sandwich Compound with Two Enveloped Nickel Atoms, J. Organomet. Chem. 122, 265–273 (1976).
G. Wilke, M. Kröner, and B. Bogdanovic, Ein Zwischenprodukt der Synthese von Cyclododecatrien aus Butadien, Angew. Chem. 73, 755–756 (1961).
B. Bogdanovic, P. Heimbach, M. Kröner, and G. Wilke, Zum Reaktionsablauf der Cyclotrimerisation von Butadien-(1.3), Liebigs Ann. Chem. 727, 143–160 (1969).
G. Wilke, B. Bogdanovic, P. Hardt, P. Heimbach, W. Keim, M. Kröner, W. Oberkirch, K. Tanaka, E. Steinrücke, D. Walter, and H. Zimmermann, Allyl-Transition Metal Systems, Angew. Chem. Int. Ed. Engl. 5, 151–164 (1966).
K. Fischer, K. Jonas, and G. Wilke, Tris(ethylene)nickel(0), Angew. Chem. Int. Ed. Engl. 12, 565–566 (1973).
C. Krüger, and Y.-H. Tsay, The Molecular and Crystal Structure of Bis(ethylene)(tricyclohexylphosphine)nickel, J. Organomet. Chem. 34, 387–395 (1972).
G. Wilke, and G. Herrmann, Ethylenebis(triphenylphosphine)nickel and Analogous Complexes, Angew. Chem. 74, 693–694 (1962).
W. A. Herrmann, 100 Years of Metal Carbonyls: a Serentipitous Chemical Discovery of Major Scientific and Industrial Impact, J. Organomet. Chem. 383, 21–44 (1990).
F. G. A. Stone, Synthetic Applications of d10 Metal Complexes, J. Organomet. Chem. 100, 257–271 (1975).
F. G. A. Stone, “Ligand-Free” Platinum Compounds, Acc. Chem. Res. 14, 318–325 (1981).
J. Müller, and P. Göser, Bis(1,5-cyclooctadiene)platinum(0), Angew. Chem. Int. Ed. Engl. 6, 364–65 (1967).
M. Green, J. A. K. Howard, J. L. Spencer, and F. G. A. Stone, Synthesis of Ethylene, Cyclo-octa-1,5-diene, Bicyclo [2.2.1]heptene, and trans-Cyclo-octene Complexes of Palladium(0) and Platinum(0); Crystal and Molecular Structure of Tris(bicyclo2.2.1]heptene)platinum, J. Chem. Soc., Dalton Trans. 1977, 271–277.
M. Green, J. A. K. Howard, M. Murray, J. L. Spencer, and F. G. A. Stone, Synthesis and Crystal and Molecular Structure of Tris-μ-(t-butylisocyanide)-tris-(t-butylisocyanide)-triangulo-triplatinum, J. Chem. Soc., Dalton Trans. 1977, 1509–1514.
N. M. Boag, M. Green, D. M. Grove, J. A. K. Howard, J. L. Spencer, and F. G. A. Stone, The Synthesis and Crystal Structure of Bis(diphenylacetylene)platinum, and Studies on Related Compounds, J. Chem. Soc., Dalton Trans. 1980, 2170–2181.
M. Green, A. Laguna, J. L. Spencer, and F. G. A. Stone, Bis(η-cyclo-octa-1,5-diene)-platinum and –palladium with Fluoroolefins, J. Chem. Soc., Dalton Trans. 1977, 1010–1016.
H. Huber, G. A. Ozin, and W. J. Power, Synthesis and Characterization of Reactive Intermediates in the Palladium Atom-Ethylene System, (C2H4)nPd (where n = 1, 2, or 3), Inorg. Chem. 16, 979–983 (1977)
R. M. Atkins, R. Mackenzie, P. L. Timms, and T. W. Turney, The Preparation of Palladium-Olefin Complexes from Palladium Vapour, J. Chem. Soc., Chem. Comm. 1975, 764.
R. Mackenzie, and P. L. Timms, Reaction of Metal Atoms with Solutions; Preparation of Bis(cyclo-octa-1,5-diene)iron(0), J. Chem. Soc., Chem. Comm. 1974, 650–651.
P. S. Skell, E. M. Van Dam, and M. P. Silvon, Reactions of Tungsten and Molybdenum Atoms with 1,3-Butadiene. Tris(butadiene)tungsten and molybdenum, J. Am. Chem. Soc. 96, 626–627 (1974).
R. E. Moriarty, R. D. Ernst, and R. Bau, Structure of Tris(methyl vinyl ketone)tungsten, J. Chem. Soc., Chem. Comm. 1972, 1242–1243.
E. O. Fischer, J. Müller, and P. Kuzel, Eine neue Synthese von Dibenzolchrom, Rev. Chim., Acad. Rep. Populaire Roumaine 7, 827–834 (1962).
E. O. Fischer, and J. Müller, Metall-π-Komplexe des Rutheniums und Osmiums mit 6- und 8-gliedrigen cyclischen Oligoolefinen, Chem. Ber. 96, 3217–3222 (1963).
J. Müller, and E. O. Fischer, Neue π-Komplexe des Eisen(0) und Ruthenium(0) mit cyclischen Olefinen, J. Organomet. Chem. 5, 275–282 (1966) , and references cited therein.
J. Müller, and B. Mertschenk, Dicycloheptatrienvanadin(0), J. Organomet. Chem. 34, C41–C42 (1972).
M. H. L. Green, P. A. Newman, and J. A. Bandy, A Comparison of the Rates of Intramolecular Hydrogen Migration in the Molecules [Mo(η-C7H8)2]n+ to give [Mo(η-C7H7)(η-C7H9)]n+, n = 0 or 1: Crystal Structures of [Mo(η-C7H8)2], [Mo(η-C7H7)(η-C7H9)], and [Mo(η-C7H8)2]BF4, J. Chem. Soc., Dalton Trans. 1989, 331–343.
P. L. Timms, and T. W. Turney, Reactions of Transition-metal Vapours with Cycloheptatriene and Cyclooctatetraene, J. Chem. Soc., Dalton Trans. 1976, 2021–2025.
F. G. N. Cloke, M. L. H. Green, and P. J. Lennon, Synthesis of d2 η-Cycloheptatrienyl-η-cycloheptadienyl-zirconium and -hafnium Using the Metal Vapours, J. Organomet. Chem. 188, C25–C26 (1980).
J. C. Green, M. L. H. Green, and N. M. Walker, Synthesis, Crystal Structure and Reactions of Zerovalent 16-Electron Bis(η-cycloheptatriene)zirconium, J. Chem. Soc., Dalton Trans. 1991, 173–180.
K. Jonas, Dilithium-nickel-olefin Complexes. Novel Bimetallic Complexes From a Transition Metal and a Main Goup Metal, Angew. Chem. Int. Ed. Engl. 14, 752–753 (1975).
K. Jonas, Reactive Organometallic Compounds Obtained from Metallocenes and Related Compounds and Their Synthetic Applications, Angew. Chem. Int. Ed. Engl. 24, 295–311 (1985).
K. Jonas, R. Mynott, C. Krüger, J. C. Sekutowski, and Y.-H. Tsay, Bis(η-1,5-cyclooctadiene)cobalt Lithium, Angew. Chem. Int. Ed. Engl. 15, 767–768 (1976).
K. Jonas, and L. Schieferstein, Simple Approach to Lithium- and Zinc-metalized η-Cyclopentadienyliron-olefin Complexes, Angew. Chem. Int. Ed. Engl. 18, 549–550 (1979).
K. Jonas, L. Schieferstein, C. Krüger, and Y.-H. Tsay, Tetrakis(ethylene)irondilithium and Bis(μ4-1,5-cyclooctadiene)irondilithium, Angew. Chem. Int. Ed. Engl. 18, 550–551 (1979).
K. Jonas, and C. Krüger, Alkali Metal-Transition Metal π-Complexes, Angew. Chem. Int. Ed. Engl. 19, 520–538 (1980).
K. Jonas, Alkali Metal-Transition Metal π-Complexes, Adv. Organomet. Chem. 19, 97–122 (1981).
K. R. Pörschke, W. Kleimann, G. Wilke, K. H. Claus, and C. Krüger, Synthesis and Structure of [Na(tmeda)2]+[HNi2(C2H4)4] –, Angew. Chem. Int. Ed. Engl. 22, 991–992 (1983).
G. J. Leigh, A Celebration of Inorganic Lives: Interview of Joseph Chatt, Coord. Chem. Rev. 108, 4–25 (1991).
C. Eaborn, and G. J. Leigh, Joseph Chatt, C.B.E., Biogr. Mem. Fellows R. Soc. 42, 95–110 (1996).
G. Wilke, Contributions to Homogeneous Catalysis 1955–1980, J. Organomet. Chem. 200, 349–364 (1980).
P. M. Maitlis, and A. F. Hill, An Interview with Peter Maitlis and A Selection of Higlights from Gordon Stone’s Research by Anthony Hill, Inorg. Chim. Acta 358, 1345–1357 (2005).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2009 Springer Science+Business Media, LLC
About this chapter
Cite this chapter
Werner, H. (2009). The Binding of Ethene and Its Congeners: Prototypical Metal π-Complexes. In: Landmarks in Organo-Transition Metal Chemistry. Profiles in Inorganic Chemistry. Springer, New York, NY. https://doi.org/10.1007/978-0-387-09848-7_7
Download citation
DOI: https://doi.org/10.1007/978-0-387-09848-7_7
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-0-387-09847-0
Online ISBN: 978-0-387-09848-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)