Planar tetracoordination of carbon in groups 4 and 5 organometallic chemistry

Accounts of Chemical Research

Volumn 32, Issue 6, 1999, Pages 494-502

  Choukroun, Robert ^a   Cassoux, Patrick ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CARBON; COPPER DERIVATIVE; METAL COMPLEX; ORGANOMETALLIC COMPOUND; TITANIUM DERIVATIVE; VANADIUM DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BINDING; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; INFRARED SPECTROSCOPY; METAL BINDING; NUCLEAR MAGNETIC RESONANCE; OXIDATION; RAMAN SPECTROMETRY; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0032817120     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970304z     Document Type: Article

References (76)

1. (a) Van't Hoff, J. H. Sur les Formules de Structure dans l'Espace. Arch. Néerl. Sci. Exactes Nat. 1874, 445-54.
2. (b) Le Bel, J. A. Bull. Soc. Chim. Fr. 1874, 22, 337-347.
3. Hoffmann, R.; Alder, R. W.; Wilcox Jr., C. F. Planar Tetracoordinate Carbon. J. Am. Chem. Soc. 1970, 92, 4992-4993.
4. Sorger, K.; Ragué Schleyer, P. V. Planar and Inherently Non-Tetrahedral Tetracoordinate Carbon: a Status Report. J. Mol. Struct. 1995, 338, 317-346.
5. (a) Seidel, W.; Kreisel, G.; Mennenga, H. Bis(2-6-dimethoxyphenyl)vanadium - a diamagnetic vanadium (II) compound. Z. Chem. 1976, 16, 492-493.
6. (b) Cotton, F. A.; Millar, F. The Probable Existence of a Triple Bond between Two Vanadium Atoms. J. Am. Chem. Soc. 1977, 99, 7886-7891.
7. (a) Erker, G. Planar-Tetracoordinate Carbon: Making Stable Anti-Van't Hoff/LeBel Compounds. Comments Inorg. Chem. 1992, 13, 111-131.
8. (b) Albrecht, M.; Erker, G.; Krüger, C. The Synthesis of Stable, Isolable Planar-Tetracoordinate Carbon Compounds. Synlett 1993, 441-448.
9. Pellny, P.-M.; Peulecke, N.; Burlakov, V. V.; Tillack, A.; Baumann, W.; Spannenberg, A.; Kempe, R.; Rosenthal, U. Twofold C-C Single Bond Activation and Cleavage in the Reaction of Octatetraynes with Titanocene and Zirconocene Complexes. Angew. Chem., Int. Ed. Engl. 1997, 36, 2615-2617.
10. Jones, W. M.; Klosin, J. Transition-Metal Complexes of Arynes, Strained Cyclic Alkynes and Strained Cyclic Cumulenes. Adv. Organomet. Chem. 1998, 42, 147-221.
11. (e) Pulst. S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal, U. The First Metathesis of C-C Single Bonds in Homogeneous Solution: Titanocene-Mediated and Photocatalyzed Cleavage and Recombination of Disubstituted Butadiynes. Angew. Chem., Int. Ed. Engl. 1998, 37, 1925-1927.
12. 5, Cl, H.; R = H, F, CN): A Theoretical Study. J. Am. Chem. Soc. 1998, 120, 6952-6964.
13. Röttger, D.; Erker, G. Compounds Containing Planar-Tetracoordinate Carbon. Angew. Chem., Int. Ed. Engl. 1997, 36, 812-827.
14. (a) Roberts, D. A.; Geoffroy, G. L. Compounds with Heteronuclear Bonds between Transition Metals. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel E. W., Eds.; Pergamon: Oxford, 1982; Vol. 6, Chapter 40.
15. (b) Stephan, D. W. Early-Late Heterobimetallics. Coord. Chem. Rev. 1989, 95, 41-107.
16. Hornton, A. D.; Orpen, A. G. A Structurally Distorted Ligand in an Electron-Deficient Dizirconocene Cation: Unusual 1, 2-and 1,1-Dimetalloalkenes. Angew. Chem., Int. Ed. Engl. 1992, 31, 876-878.
17. 4. Angew. Chem., Int. Ed. Engl. 1993, 32, 1623-1625.
18. (b) Röttger, D.; Erker, G.; Fröhlich, R.; Grehl, M.; Silverio, S. J.; Hyla-Kryspin, I.; Gleiter, R. Determination of the Stabilization Energy of Planar-Tetracoordinate Carbon in Dynamic Dinuclear (μ-hydrocarbyl)bis(zirconocene) Cation Complexes and Detection of an Organometallic Memory Effect in their Formation. J. Am. Chem. Soc. 1995, 117, 10503-10512.
19. Röttger, D.; Erker, G.; Fröhlich, R.; Kotila, S. Stabilization of a Planar-Tetracoordinate Carbon Center in an Organometallic Complex Containing both a Zirconocene and a Hafnocene Moiety. Chem. Ber. 1996, 129, 1-3.
20. Pulst, S.; Arndt, P.; Heller, B.; Baumann, W.; Kempe, R.; Rosenthal, U. Nickel(0) Complexes of Five-Membered Titana-and Zirconacyclocumulenes as Intermediates in the Cleavage of C-C Bonds of Disubstituted Butadiynes. Angew. Chem., Int. Ed. Engl. 1996, 35, 1112-1114.
21. Rosenthal, U.; Ohff, A.; Baumann, W.; Kempe, R.; Tillack, A.; Burlakov, V. V. Synthesis and Structure of the Smallest Cyclic Cumulene; Reaction of 1,3-Diynes with Zirconocene Complexes. Angew. Chem., Int. Ed. Engl. 1994, 33, 1605-1607.
22. Chisholm, M. H. Metalla-enes and Metalla-ynes. From Small Molecules to Infinite Polymers. Angew. Chem., Int. Ed. Engl. 1991, 30, 673-674.
23. (a) Nast, R. Coordination Chemistry of Metal Alkynyl Compounds. Coord. Chem. Rev. 1982, 47, 89-124.
24. (b) Lotz, S.; Van Rooyen, P. H.; Meyer, R. σ,π-Bridging Ligands in Bimetallic and Trimetallic Complexes. Adv. Organomet. Chem. 1995, 37, 219-313.
25. IR] Units (M = Cu, Ag). Coord. Chem. Rev. 1995, 143, 113-168.
26. (a) Burlakov, V. V.; Rosenthal, U.; Petrovskii, V. V.; B. Shur, V.; Vol'pin, E. Complex of Titanocene with Bis(trimethylsilyl) Acetylene. Metalloorg. Khim. 1988, 1, 953-954.
27. (b) Rosenthal, U.; Görls, H.; Burlakov, V. V.; Shur, V. B.; Vol'pin, E. Alkinkomplexe des Titanocens und Permethyltitanocens ohne zusätzliche Liganden - Erste Strukturvergleiche. J. Organomet. Chem. 1992, 426, C53-C57.
28. 3). J. Organomet. Chem. 1995, 501, 179-188.
29. 3). Z. Anorg. Allg. Chem. 1995, 627, 77-83.
30. 3). J. Organomet. Chem. 1995, 501, 189-194.
31. Burlakov, V. V.; Ohff, A.; Lefeber, C.; Tillack, A.; Baumann, W.; Kempe, R.; Rosenthal, U. The First Titanacyclic Five-Membered Cumulene. Synthesis, Structure, and Reactivity. Chem. Ber. 1995, 128, 967-971.
32. (a) Lang, H.; Seyfert, D. Synthese und Reaktivität von Alkinyl-substituierten Titanocen-Komplexen. Z. Naturforsch. 1990, 45b, 212-220.
33. (b) Janssen, M.; Herres, M.; Zsolnai, L.; Grove, D. M.; Spek, A. L.; Lang, H.; van Koten, G. A Stable Bimetallic Copper-(I) Titanium Acetylide. Organometallics 1995, 14, 1098-1100.
34. 3)] CuBr. Inorg. Chem. 1996, 35, 6266-6272.
35. 1-Bonded Alkyl, Vinyl and Aryl Ligands. J. Am. Chem. Soc. 1996, 118, 4817-4829 and references therein.
36. Schottek, J.; Erker, G.; Fröhlich, R. Formation of Metallocene-Stabilized Planar-Tetracoordinate Carbon Compounds by a Protonation Route. Eur. J. Inorg. Chem. 1998, 551-558.
37. 2] Containing Two Planar-Tetracoordinate Carbon Atoms. Chem. Eur. J. 1998, 4, 1100-1105.
38. Danjoy, C. Complexes du titane et du vanadium. Vers le système céramique quaternaire V.Ti.C.N par dépôt chimique en phase vapeur. Ph.D. Thesis, Institut National Polytechnique de Toulouse, France, 1996, No. 1197.
39. Valade, L.; Choukroun, R.; Danjoy, C.; Chansou, B.; De Caro, D.; Cassoux, P. Possibilités d'obtention de dépôts dans le système céramique Ti-V-C-N à partir de sources moléculaires. Ann. Chim. Sci. Mater. 1998, 23, 721-732.
40. 2]. Organometallics 1990, 9, 1982-1987 and references therein.
41. (b) Trzeciak, A. M.; Ziolkowski, J. J.; Choukroun, R. New Bimetallic Rhodium-Zirconium Catalysts for Homogeneous Olefin Hydroformylation. J. Mol. Catal. 1996, 110, 135-139 and references therein.
42. 9] (x = 0, 15). Z. Anorg. Allg. Chem. 1987, 546, 21-32.
43. Mazzanti, M.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. (N,N′-Ethylenebis(acetylacetone iminato))vanadium(III) Derivatives: Syntheses and Substitution Reactions at the V-Cl Bond. Inorg. Chem. 1986, 25, 4158-4164.
44. 2V and its Chromium Analog. Organometallics 1995, 14, 4043-4045.
45. Teuben, J. H.; De Liefde Meijer, H. J. Phenylethynyl Complexes of Titanocene and Vanadocene. J. Organomet. Chem. 1969, 17, 87-93.
46. (a) Erker, G.; Frömberg, W.; Mynott, R.; Gabor, B.; Krüger, C. Unusual Bridging of the Metal Centers in Dimeric Bis(η-methylcyclopentadienyl)-phenylethynylzirconium. Angew. Chem., Int. Ed. Engl. 1986, 98, 463-464.
47. (b) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Angermund, K.; Krüger, C. π-Conjugation and Dynamic Behavior in Doubly Acetylide-Bridged Binuclear Group 4 Bent Metallocene Complexes. Organometallics 1989, 8, 911-920.
48. 5-cyclopentadienyl)-Bis(alkynyl)zirconium(IV) Complexes. J. Organomet. Chem. 1979, 182, 353-359.
49. (a) Warner, B. P.; Davis, W. M.; Buchwald, S. L. Synthesis and X-ray Structure of a Zirconocene Complex of Two Alkynes. J. Am. Chem. Soc. 1994, 116, 5471-5472.
50. 2 with Zirconocene Complexes: Cleavage of the Central C-C Single Bond to Form Symmetrically and Unsymmetrically Doubly Acetylide-Bridged Metallocene Complexes. Organometallics 1994, 13, 2903-2906.
51. + (M = Li, Na, K and Cs). J. Organomet. Chem. 1996, 515, 57-64.
52. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Unusual Reactions of Titanocene-and Zirconocene-Generating Complexes. Synlett 1996, 2, 111-118.
53. (e) Rosenthal, U.; Ohff, A.; Baumann, W.; Kempe, R.; Tillack, A.; Burlakov, V. V. Synthesis and Structure of the Smallest Cyclic Cumulene; Reaction of 1,3-Diynes with Zirconocene Complexes. Angew. Chem., Int. Ed. Engl. 1994, 33, 1605-1607.
54. 2-alkyne-Titanocene and -Zirconocene Complexes - Influence of Metals, Alkyne Substituents, Cp Substitution and Additional Ligands. Eur. J. Inorg. Chem. 1998, 419-424.
55. (a) Sekutowski, D.; Stucky, G. D. Oxidative Coupling of the Phenylethynyl Group in μ-(1-3η:2-4η-trans,-trans-1,4-Diphenylbutadiene)-bis(bis(η5- Methylcy-clopentadienyl) Titanium) and the Reaction of 1,4-Diphenyl-1,3-Butadiene with Bis(cyclopentadienyl)titanium(II). J. Am. Chem. Soc. 1976, 98, 1376-1382.
56. 2-Dimethyl Acetylenedicarboxylato-C,C)bis(η-Cyclopentadienyl) Vanadium. Inorg. Chem. 1979, 18, 2282-2287.
57. Petersen, J. L.; Griffith, L. Electron Paramagnetic Resonance and Structural Studies of Small-Ring Metallacycles. Bonding in a Metallacyclopropene Formed by the Oxidative Addition of an Acetylene to Vanadocene. Inorg. Chem. 1980, 19, 1852-1858.
58. 1-Complexes of Biscyclopentadienylvanadium. Russ. Chem. Rev. 1985, 54, 724-738 (translated from Usp. Khim. 1985, 54, 1235-1259).
59. 1-Complexes of Biscyclopentadienylvanadium. Russ. Chem. Rev. 1985, 54, 724-738 (translated from Usp. Khim. 1985, 54, 1235-1259).
60. Zhao, J.; Valade, L.; Choukroun, R.; Cassoux, P. Unpublished results.
61. (a) Janssen, M. D.; Herres, M.; Zsolnai, L.; Grove, D. M.; Spek, A. L.; Lang, H.; van Koten, G. A Stable Bimetallic Copper(I) Titanium Acetylide. Organo-metallics 1995, 14, 1098-1100.
62. (b) Yasufuku, K.; Yamazaki, H. Novel route to mixed transition-metal complexes. Bull. Chem. Soc. Jpn. 1972, 45, 2664.
63. 1 Complexes: Structure and Magnetism. J. Chem. Soc., Chem. Commun. 1997, 2315-2316.
64. Takahaski, T.; Nishihara, Y.; Sun, W.-H.; Fischer, R.; Nakajima, K. Reaction of Alkenylzirconocenes with Dialkylzirconocenes: Unexpected Formation of Bimetallic (μ-alkynyl)zirconocene Complexes. Organometallics 1997, 16, 2216-2219.
65. 4-Conjugated Diene-Zirconocene Complexes. J. Am. Chem. Soc. 1980, 102, 6344-6346.
66. Buchwald, S. L.; Watson, B. T.; Huffman, J. C. The Synthesis, Reactions, and Molecular Structure of Zirconocene-alkyne Complexes. J. Am. Chem. Soc. 1987, 109, 2544-2546.
67. Hunter, W. E.; Hrncir, D. C.; Vann Bynum, R.; Penttila, R. A.; Atwood, J. L. The Search for Dimethylzirconocene. Crystal Structures of Dimethylzirconocene, Dimethylhafnocene, and (μ-Oxo)-bis(methylzirconocene. Organometallics 1983, 2, 750-755.
68. 2(s-trans-PhCH=CH-CH=CHPh). J. Chem. Soc., Chem. Commun. 1982, 191-192.
69. Donnadieu, B.; Choukroun, R.; Cassoux, P. Unpublished results.
70. (a) Binger, P.; Podubrin, S. Metallocene(II) Complexes of Zirconium and Hafnium. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G., Wilkinson G., Eds.; Pergamon Press: Fort Collins, 1995; Vol. 4, pp 439-463.
71. (b) Broene, R. D. Transition Metal Alkyl Complexes: Reductive Dimerization of Alkenes and Alkynes. Ibid.; Vol. 12, pp 323-347.
72. Buchwald, S. L.; Broene, R. D. Transition Metal Alkyne Complexes: Zirconium-benzyne Complexes. Ibid.; pp 771-784.
73. Temme, B.; Erker, G.; Frölich, R.; Grehl, M. Heterodimetal-Betaine Chemistry: Catalytic and Stoichiometric Coupling of Alkynyl Ligands under the Joint Influence of Zirconium and Boron Centers. Angew. Chem., Int. Ed. Engl. 1994, 33, 1480-1482.
74. Burlakov, V. V.; Peulecke, N.; Baumann, W.; Spannenberg, A.; Kempe, R.; Rosenthal, U. Reactions of the Phenyl-Substituted Five-Membered Titanacyclocumulene. Unusual Coupling of a 1,4-Disubstituted 1,3-Butadiyne with Two Titanium Atoms. J. Organomet. Chem. 1997, 536-537, 293-297.
75. Rosenthal, U.; Pulst, S.; Arndt, P.; Ohff, A.; Tillack, A.; Baumann, W.; Kempe, R.; Burlakov, V. V. Heterobimetallic σ,π-Acetylide-Bridged Complexes from Disubstituted 1,3-Butadiynes. Organometallics 1995, 14, 2961-2968.
76. This catalytic conversion is also observed in the absence of light.