An investigation of carbon-fluorine bond functionalization. Versatile reactivity of tungsten(II) fluoride carbonyl metallacycles with alkynes

Organometallics

Volumn 15, Issue 25, 1996, Pages 5292-5301

  Kiplinger, Jaqueline L ^a   King, Margaret A ^a   Fechtenkötter, Andreas ^a   Arif, Atta M ^a   Richmond, Thomas G ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007819052     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960561s     Document Type: Article

References (70)

1. (a) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373-431.
2. (b) Harrison, R. G.; Richmond, T. G. J. Am. Chem. Soc. 1993, 115, 5303-5304.
3. (c) Bennett, B. K.; Harrison, R. G.; Richmond, T. G. J. Am. Chem. Soc. 1994, 116, 11165-11166.
4. (d) Kiplinger, J. L.; Richmond, T. G. J. Am. Chem. Soc. 1996, 118, 1805-1806.
5. (e) Kiplinger, J. L.; Richmond, T. G. Chem. Commun. 1996, 1115-1116.
6. (a) Osterberg, C. E.; King, M. A.; Arif, A. M.; Richmond, T. G. Angew. Chem., Int. Ed. Engl. 1990, 29, 888-890.
7. (b) Richmond, T. G. Coord. Chem. Rev. 1990, 105, 221-250.
8. (c) Lucht, B. L.; Poss, M. J.; King, M. A.; Richmond, T. G. J. Chem. Soc., Chem. Commun. 1991, 400-401.
9. 2-vinyl complexes, cis describes the stereochemistry between the inserted alkyne and the fluoride ligand.
10. Osterberg, C. E.; Richmond, T. G. ACS Symp. Ser. 1994, 555, 392-404.
11. (a) Anderson, C. M.; Crespo, M.; Jennings, M. C.; Lough, A. J.; Ferguson, G.; Puddephatt, R. J. Organometallics 1991, 10, 2671-2679.
12. (b) Anderson, C. M.; Crespo, M.; Ferguson, G.; Lough, A. J.; Puddephatt, R. J. Organometallics 1992, 11, 1177-1181.
13. (c) Crespo, M.; Martinez, M.; Sales, J. Organometallics 1993, 12, 4297-4304.
14. (a) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum: New York, 1994.
15. (b) Chemistry of Organic Fluorine Compounds II. A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; and references therein.
16. (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd ed.; Wiley: New York, 1972.
17. (b) Park, S.; Roundhill, D. M. Inorg. Chem. 1989, 28, 2905-2906.
18. (c) Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. J. Am. Chem. Soc. 1993, 115, 356-357.
19. (d) Vincente, J.; Chicote, M. T.; Fernandez-Baeza, J.; Fernandez-Baeza, A.; Jones, P. G. J. Am. Chem. Soc. 1993, 115, 794-796.
20. (a) Usón, R.; Fornies, J.; Espinet, P.; Garcia, A.; Foces-Foces, C; Cano, F. J. Organomet. Chem. 1985, 282, C35-C38.
21. (b) Park, S.; Pontier-Johnson, M.; Roundhill, D. M. J. Am. Chem. Soc. 1989, 111, 3101-3103.
22. Burdenuic, J.; Chupka, W.; Crabtree, R. H. J. Am. Chem. Soc. 1995, 117, 10119-10120.
23. (a) Wu, G.; Rheingold, A. L.; Heck, R. F. Organometallics 1986, 5, 1922-1924.
24. (b) Maassarani, F.; Pfeffer, M.; Le Borgne, G. Organometallics 1987, 6, 2029-2042; and references therein.
25. (c) Grigsby, W. J.; Main, L.; Nicholson, B. K. Organometallics 1993, 12, 397-407.
26. Kiplinger, J. L.; King, M. A.; Arif, A. M.; Richmond, T. G. Organometallics 1993, 12, 3382-3384.
27. Shriver, D. F.; Drezdon, M. A. Manipulation of Air Sensitive Compounds, 2nd ed.; Wiley: New York, 1986
28. Kiplinger, J. L.; Richmond, T. G.; Arif, A. M.; Dücker-Benfer, C.; van Eldik, R. Organometallics 1996, 15, 1545-1564.
29. Cetinkaya, B.; Lappert, M. F.; McMeeking, J.; Palmer, D. E. J. Chem. Soc., Dalton Trans. 1973, 1202-1208.
30. Frenz, B. A. The Enraf-Noníus CAD 4 SPD - A Real-Time System for Concurrent X-ray Data Collection and Crystal Structure Determination. In Computing and Crystallography; Schenk, H., Olthof-Hazenkamp, R., van Konigsveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, Holland, 1978; pp 64-71.
31. Comer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England, 1974; Vol. IV, Tables 2.2B and 2.3.1, pp 72-98, 149-150.
32. (a) Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1988.
33. 13C NMR Data for Organometallic Compounds; Academic Press: New York, 1981.
34. (a) Kiplinger, J. L.; Richmond, T. G. Polyhedron, in press.
35. (b) Looman, S. D.; Giese, S.; Arif, A. M.; Richmond, T. G. Polyhedron 1996, 15, 2809-2811.
36. Templeton, J. L.; Ward, B. C. J. Am. Chem. Soc. 1980, 102, 3288-3290.
37. (a) Blake, A. J.; Cockman, R. W.; Ebsworth, E. A. V.; Holloway, J. H. J. Chem. Soc., Chem. Commun. 1988, 529-530.
38. (b) Darensbourg, D. J.; Klausmeyer, K. K.; Reibenspies, J. H. Inorg. Chem. 1995, 34, 4933-4934.
39. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
40. 4 alkyne complexes, see: Templeton, J. L. Adv. Organomet. Chem. 1989, 29, 1-100.
41. (a) Allen, S. R.; Baker, P. K.; Barnes, S. G.; Botrill, M.; Green, M.; Orpen, G. A.; Welch, A. J. J. Chem. Soc., Dalton Trans. 1983, 927-939.
42. (b) Reger, D. L. Acc. Chem. Res. 1988, 21, 229-235.
43. March, J. Advanced Organic Chemistry, 2nd ed.; Wiley: New York, 1985; Chapter 9.
44. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
45. Allen, S. R.; Beevor, R. G.; Green, M.; Norman, N. C.; Orpen, A. G.; Williams, I. D. J. Chem. Soc., Dalton Trans. 1985, 435-450.
46. Gamble, A. S.; White, P. S.; Templeton, J.-L. Organometallics 1991, 10, 693-702.
47. (a) Davidson, J. L.; Wilson, W. F.; Manjlovic-Muir, L.; Muir, K. W. J. Organomet. Chem. 1983, 254, C6-C10.
48. (b) Carlton, L.; Davidson, J. L.; Miller, J. C.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1984, 11-13.
49. (c) Carlton, L.; Davidson, J. L. J. Chem. Soc., Dalton Trans. 1987, 895-905.
50. (d) Agh-Atabay, N. M.; Canoira, L. J.; Carlton, L.; Davidson, J. L. J. Chem. Soc., Dalton Trans. 1991, 1175-1182.
51. (a) Gates, B. C.; Katzer, J. R.; Schuit, G. C. A. Chemistry of Catalytic Processes; McGraw-Hill: New York, 1979.
52. (b) Carlton, L.; Davidson, J. L.; Ewing, P.; Manjlovic-Muir, L.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1985, 1474-1476.
53. (c) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis. 2nd ed.; Wiley-Interscience: New York, 1992.
54. (a) Green, M.; Norman, N. C.; Orpen, A. G. J. Am. Chem. Soc. 1981, 103, 1267-1269.
55. (b) Allen, S. R.; Green, M.; Orpen, A. G.; William, I. D. J. Chem. Soc., Chem. Commun. 1982, 826-828.
56. (c) Beevor, R. G.; Green, M.; Orpen, A. G.; Williams, I. D. J. Chem. Soc., Chem. Commun. 1983, 673-675.
57. (d) Feng, S. G.; Templeton, J. L. Organometallics 1992, 11, 2168-2175.
58. (e) Feng, S. G.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1992, 114, 2951-2960.
59. Davidson, J. L. J. Organomet. Chem. 1985, 186, C19-C22.
60. Davidson, J. L.; Vasapollo, G.; Manjlovic-Muir, L.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1982, 1025-1027.
61. (a) Davidson, J. L.; Murray, I. E. P.; Preston, P. N.; Russo, M. V. J. Chem. Soc., Chem. Commun. 1981, 1059-1061.
62. (b) Davidson, J. L.; Murray, I. E. P.; Preston, P. N.; Russo, M. V. J. Chem. Soc., Dalton Trans. 1983, 1783-1787.
63. Morrow, J. R.; Tonker, T. L.; Templeton, J. L. J. Am. Chem. Soc. 1985, 107, 6956-6963.
64. (a) Gipson, S. L.; Kneten, K. Inorg. Chim. Acta 1989, 157, 143-145.
65. (b) Albéniz, A. C.; Foces-Foces, C.; Cano, F. H. Organometallics 1990, 9, 1079-1085.
66. (c) Albéniz, A. C.; Espinet, P. Organometallics 1991, 10, 2987-2988.
67. Albéniz, A. C.; Espinet, P.; Jeannin, Y.; Philoche-Levisalles, M.; Mann, B. E. J. Am. Chem. Soc. 1990, 112, 6594-6600.
68. Kiplinger, J. L.; Arif, A. M.; Richmond, T. G. Inorg. Chem. 1995, 34, 399-401.
69. (a) Bahsoun, A.; Dehand, J.; Pfeffer, M.; Zinsius, M.; Bouaoud, S. E.; Le Borgne, G. J. Chem. Soc., Dalton Trans. 1979, 547-556.
70. (b) Arlen, C.; Pfeffer, M.; Fischer, J.; Mitschler, A. J. Chem. Soc., Chem. Commun. 1983, 928-929.