Organometallic chemistry of fluorinated propadienes and butadienes

Journal of Fluorine Chemistry

Volumn 125, Issue 6, 2004, Pages 853-861

  Lentz, Dieter ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

C F bond activation; Fluoroalkenes; Fluorobutadienes; Fluoropropadienes; Metal complexes

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALLENE DERIVATIVE; CARBON; FLUORINE; LIGAND; ORGANOFLUORINE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM; VINYL DERIVATIVE;

ACIDITY; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION; FLUORINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; REVIEW; SYNTHESIS; X RAY DIFFRACTION;

EID: 3242766120     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2004.02.018     Document Type: Review

References (102)

1. Schmiegel W.W. ACS Monogr. 187 1995 1101 1118
2. Ameduri B. Boutevin B. J. Fluorine Chem. 104 2000 53 62
3. J. Scheirs, Modern Fluoropolymers, Wiley, Excel Pas Victoria, Australia, 1997
4. G. Hougham, K. Johns, P.E. Casidy, T. Davidson, Fluoropolymers: Synthesis and Properties, Plenum Press, New York, 1999.
5. Smart B.E. ACS Monogr. 187 1995 979 1010
6. A complete issue of Chemical Reviews is dedicated to alkene polymerization catalysts, Chem. Rev. 100 (2000) 1167
7. Böhm L.L. Angew. Chem. 115 2003 5162 5183
8. Böhm L.L. Angew. Chem. Int. Ed. Engl. 42 2003 5010 5030
9. Britovsek G.J.P. Gibson V.C. Wass D.F. Angew. Chem. 111 1999 448-468
10. Britovsek G.J.P. Gibson V.C. Wass D.F. Angew. Chem Int. Ed. Engl. 38 1999 428 447
11. Abbenhuis H.C.L. Angew. Chem. 111 1999 1125-1127
12. Abbenhuis H.C.L. Angew. Chem Int. Ed. Engl. 38 1999 1058-1060
13. C. Elschenbroich, A. Salzer, Organometallchemie, Teubner, Stuttgart, 1986
14. J.P. Collman, C. Elschenbroich, A. Salzer, Organometallics, second ed., VCH, Weinheim, 1992
15. L.S. Hegedus, J.R. Norton, R.G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987.
16. J.A. Evans, D.R. Russell, J. Chem. Soc. Chem. Commun. (1971) 197-198
17. Howard J.A.K. Mitrprachachon P. Roy A. J. Organomet. Chem. 235 1982 375 381
18. Guggenberger L.J. Cramer R. J. Am. Chem. Soc. 94 1972 3779-3786
19. M. Green, J.A.K. Howard, J.L. Spencer, F.G.A. Stone, J. Chem. Soc. Chem. Commun. (1975) 449-451
20. J. Browning, B.R. Penfold, J. Chem. Soc. Chem. Commun. (1973) 198-199.
21. Burch R.R. Harlow R.L. Ittel S.D. Organometallics 6 1987 982-987
22. A.K. Burrel, G.R. Clark, C.E.F. Rickard, W.R. Roper, A.H. Wright, J. Chem. Soc. Dalton Trans. (1991) 609-614
23. Burrel A.K. Clark G.R. Rickard C.E.F. Roper W.R. Ware D.C. J. Organomet. Chem. 398 1990 133-158
24. Rice N.C. Oliver J.D. Acta Crystallogr. Sect. B 34 1978 3748-3751
25. Curnow O.J. Hughes R.P. Rheingold A.L. J. Am. Chem. Soc. 114 1992 3153-3155
26. J.A. Ibers, J.C. McGinnety, N. Kime, in: Proceedings of the 10th International Conference Coordination Chemistry, 1967, 93
27. Brothers P.J. Burrell A.K. Clark G.R. Rickard C.E.F. Roper W.R. J. Organomet. Chem. 394 1990 615-642
28. Kaschube W. Schröder W. Pörschke K.R. Angermund K. Krüger C.J. J. Organomet. Chem. 389 1990 399-408
29. D.R. Russel, P.A. Tucker, J. Chem. Soc. Dalton Trans. (1975) 1752-1757
30. P.B. Hitchcock, M. McPartlin, R. Mason, J. Chem. Soc. Chem. Commun. (1969) 1367-1368
31. Curnow O.J. Hughes R.P. Mairs E.N. Rheingold A.L. Organometallics 12 1993 3102-3108
32. Francis J.N. McAdam A. Ibers J.A. J. Organomet. Chem. 29 1971 131-147
33. Baraban J.M.J. McGinnety A. J. Am. Chem. Soc. 97 1975 4232-4237
34. J.A.K. Howard, S.A.R. Knox, N.J. Terrill, M.T. Yates, J. Chem. Soc. Chem. Commun. (1989) 640-642.
35. Hughes R.P. Rose P.R. Zheng X. Rheingold A.L. Organometallics 14 1995 2407-2414
36. M. Green, A.J. Osborn, F.G.A. Stone, J. Chem. Soc. A (1968) 2525-2530
37. R.L. Hunt, D.M. Roundhill, G. Wilkinson, J. Chem. Soc. A (1967) 982-984
38. P.B. Hitchcock, R. Mason, J. Chem. Soc. Chem. Commun. (1967) 242
39. Hughes R.P. Rose P.R. Rheingold A.L. Organometallics 12 1993 3109-3117
40. Hughes R.P. Adv. Organomet. Chem. 31 1990 183-267
41. R.P. Hughes, O.J. Curnow, P.R. Rose, X. Zheng, E.N. Mairs, A. Rheingold, in: J.S. Thrasher, S.H. Strauss (Eds.), Inorganic Fluorine Chemistry, ACS Symposium Series 555, Washington, DC, 1994
42. Treichel P.M. Stone F.G.A. Adv. Organomet. Chem. 1 1964 143-220
43. Richmond T.G. Angew. Chem. 112 2000 3378-3380
44. Richmond T.G. Angew. Chem Int. Ed. Engl. 39 2000 3241-3243
45. Burdeniuc J. Jedlicka B. Crabtree R.H. Chem. Ber./Recueil 130 1997 145-154
46. Kiplinger J.L. Richmond T.G. Osterberg C. Chem. Rev. 94 1994 373-431
47. Horváth I.T. Rabái J. Science 266 1994 72-75
48. Horváth I.T. Acc. Chem. Res. 31 1998 641-650
49. Fish R.H. Chem. Eur. J. 5 1999 1677-1680
50. J.L. Anderson, US Patent 2,733,278 (1956)
51. Blomquist A.T. Longone D.T. J. Am. Chem. Soc. 79 1957 4981-4982
52. Knoth W.H. Coffman D.D. J. Am. Chem. Soc. 82 1960 3873-3875
53. Dolbier W.R. Jr. Burckholder C.R. Piedrahita C.A. J. Fluorine Chem. 20 1982 637-647
54. Dolbier W.R. Jr. Acc. Chem. Res. 24 1991 63-69
55. Ogata T. Fujii K. Yoshikawa M. Hirota F. J. Am. Chem. Soc. 109 1987 7639-7641
56. Durig J.R. Li Y.S. Tong C.C. Zens A.P. Ellis P.D. J. Am. Chem. Soc. 96 1974 3805-3809
57. Domelsmith L.N. Houk K.N. Piedrahita C. Dolbier W.J. J. Am. Chem. Soc. 100 1978 6908-6911
58. Jacobs T.L. Bauer R.S. J. Am. Chem. Soc. 81 1959 606-610
59. R.E. Banks, R.N. Haszeldine, D.R. Taylor, J. Chem. Soc. (1965) 978-990
60. R.E. Banks, M.G. Barlow, R.N. Haszeldine, D.R. Taylor, J. Chem. Soc. C (1969) 1104-1107
61. Banks R.E. Haszeldine R.N. Taylor D.R. J. Fluorine Chem. 10 1977 487-493
62. Zens A.P. Ellis P.D. Ditchfield R. J. Am. Chem. Soc. 96 1974 1309-1312
63. Lu H. Friedrich B. Burton D.J. J. Fluorine Chem. 75 1995 83-86
64. Buschmann J. Koritsánszky T. Lentz D. Luger P. Nickelt N. Willemsen S. Z. Kristallogr. 215 2000 487-494
65. Dixon D.A. Smart B.E. J. Phys. Chem. 93 1989 7772-7780
66. Dewar M.J.S. Bull. Soc. Chim. Fr. 18 1951 C71-C79
67. J. Chatt, L.A. Duncunson, J. Chem. Soc. (1953) 2939-2947.
68. Albright T.A. Hoffmann R. Thibeault J.C. Thorn D.L. J. Am. Chem. Soc. 101 1979 3801-3820
69. D.M.P. Mingos, Comprehensive organometallic chemistry, in: G. Wilkinson, E. Abel, F.G.A. Stone (Eds.), vol. 3, Pergamon Press, Oxford, 1983, Chapter 19, 1
70. renking G. röhlich N. Chem. Rev. 100 2000 717-774
71. Lentz D. Willemsen S. Organometallics 18 1999 3962-3964
72. Lentz D. Nickelt N. Willemsen S. Chem. Eur. J. 8 2002 1205-1217
73. B.L. Mann, Comprehensive organometallic chemistry, in: G. Wilkinson, E. Abel, F.G.A. Stone (Eds.), vol. 3, Pergamon, Oxford, 1983, Chapter 20, p. 89; ΔG# = 35.1 kJ mol-1 was reported for CpMn(CO)2(C2H4), H. Alt, M. Herberhold, C.G. Kreiter, H. Strack, J. Organomet. Chem. 77 (1974) 353-367.
74. S. Willemsen, Dissertation, Freie Universität Berlin, Berlin, 1999.
75. Foxman B. Marten D. Rosan A. Rosenblum M. J. Am. Chem. Soc. 99 1977 2160-2165
76. Nishidi H. Takada N. Yoshimura M. Takaki T. Kobayashi H. Bull. Chem. Soc. Jpn. 57 1984 2600-2604
77. Buschmann W.E. Miller J.S. Chem. Eur. J. 4 1998 1731-1737
78. Reed C.A. Acc. Chem. Res. 31 1998 133-139
79. Strauss S.H. Chem. Rev. 93 1993 927-942
80. D. Lentz, B. Füger, A. Grommek, S. Schwede, in press.
81. Lentz D. Willemsen S. Angew. Chem. 113 2001 2142
82. Lentz D. Willemsen S. Angew. Chem. Int. Ed. Engl. 40 2001 2087
83. Lentz D. Patzschke M. Bach A. Scheins S. Luger P. Org. Biomol. Chem. 1 2003 409-414
84. D. Lentz, M. Patzschke, Z. Anorg. Allg. Chem (2004) in press.
85. Lentz D. Willemsen S. J. Organomet. Chem. 641 2002 215-219
86. Lentz D. Michael-Schulz H. Inorg. Chem. 29 1990 4396-4401
87. Lentz D. Michael H. Chem. Ber. 121 1988 1413-1416
88. Lentz D. Coord. Chem. Rev. 143 1995 383-406
89. Park J.D. Abrams J. Hein M. Gray D.N. Lacher J.K. J. Org. Chem. 23 1958 1661-1665
90. F. Diederich, P.J. Stang (Eds.), Metal Catalyzed Cross-Coupling Reactions, Wiley, VCH, Weinheim, 1998
91. P. Knochel, in: M. Beller, C. Bolm (Eds.), Transition Metals for Organic Synthesis, Hrsg, vol. 1, Wiley, VCH, Weinheim 1998.
92. Bach A. Lentz D. Luger P. Messerschmidt M. Olesch C. Patzschke M. Angew. Chem. 114 2002 311-314
93. Bach A. Lentz D. Luger P. Messerschmidt M. Olesch C. Patzschke M. Angew. Chem. Int. Ed. Engl. 41 2002 296-299
94. Nguyen B.V. Burton D.J. J. Org. Chem. 62 1997 7758-7764
95. Casado A.L. Espinet P. J. Am. Chem. Soc. 120 1998 8978-8985
96. Matsuo N. Kende A.S. J. Org. Chem. 53 1988 2304-2308
97. Lentz D. J. Chem. Crystallogr. 33 2003 977-981
98. D. Lentz, F. Akkermann, R. Kickbusch, M. Patzschke, Angew. Chem. submitted.
99. G.S. Girolami, R.J. Morris, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II: a Review of the Literature 1982-1994, vol. 6, Elsevier, Exeter, 1995; for a review on organometallic oxides of main group and transition elements see, H.W. Roesky, I. Haiduc, N.S. Hosmane, Chem. Rev. 103 (2003) 2579-2596.
100. Schardt B.C. Hollander F.J. Hill C.L. J. Am. Chem. Soc. 104 1982 3964-3972
101. Martin E.L. Sharkey W.H. J. Am. Chem. Soc. 81 1959 5256-5258
102. Hughes R.P. Laritchev R.B. Zakharov L.N. Rheingold A.L. J. Am. Chem. Soc. 126 2004 2308-2309