α-CH bond activation of coordinated Et2O via reaction of PR3 (R = Ph, Cy) with the cationic complex [C5Me5W(CO)3(OEt2)]+

Organometallics

Volumn 15, Issue 1, 1996, Pages 2-4

  Yi, Chae S ^a   Wódka, Dariusz ^a   Rheingold, Arnold L ^b   Yap, Glenn P A ^b  

^a Marquette University   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013531178     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950790z     Document Type: Article

References (43)

1. For recent reviews, see: (a) Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6. (b) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 3. (c) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8. (d) Masamune, S.; McCarthy, P. A. In Macrolide Antibiotics; Omura, S., Ed.; Academic Press: New York, 1984. (e) Recent Progress in the Chemical Synthesis of Antibiotics; Lukas, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990.
2. For recent reviews, see: (a) Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6. (b) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 3. (c) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8. (d) Masamune, S.; McCarthy, P. A. In Macrolide Antibiotics; Omura, S., Ed.; Academic Press: New York, 1984. (e) Recent Progress in the Chemical Synthesis of Antibiotics; Lukas, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990.
3. For recent reviews, see: (a) Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6. (b) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 3. (c) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8. (d) Masamune, S.; McCarthy, P. A. In Macrolide Antibiotics; Omura, S., Ed.; Academic Press: New York, 1984. (e) Recent Progress in the Chemical Synthesis of Antibiotics; Lukas, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990.
4. For recent reviews, see: (a) Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6. (b) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 3. (c) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8. (d) Masamune, S.; McCarthy, P. A. In Macrolide Antibiotics; Omura, S., Ed.; Academic Press: New York, 1984. (e) Recent Progress in the Chemical Synthesis of Antibiotics; Lukas, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990.
5. For recent reviews, see: (a) Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6. (b) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 3. (c) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8. (d) Masamune, S.; McCarthy, P. A. In Macrolide Antibiotics; Omura, S., Ed.; Academic Press: New York, 1984. (e) Recent Progress in the Chemical Synthesis of Antibiotics; Lukas, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990.
6. Godfrey, C. R. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7.
7. (a) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992.
8. (b) Elschenbroich, C.; Salzer, A. Organometallics: A Concise Introduction; VCH: New York, 1989.
9. For recent selected examples, see: (a) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405. (b) Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenziger, N. Organometallics 1989, 8, 2892 and references therein. (c) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (d) Caldarelli, J. L.; Wagner, L. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 2878. (e) Hauptman, E.; Brookhart, M.; Fagan, P. J.; Calabrese, J. C. Organometallics 1994, 13, 774. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137. (g) Vaughan, W. M.; Abboud, K. A.; Boncella, J. M. Organometallics 1995, 14, 1567.
10. For recent selected examples, see: (a) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405. (b) Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenziger, N. Organometallics 1989, 8, 2892 and references therein. (c) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (d) Caldarelli, J. L.; Wagner, L. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 2878. (e) Hauptman, E.; Brookhart, M.; Fagan, P. J.; Calabrese, J. C. Organometallics 1994, 13, 774. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137. (g) Vaughan, W. M.; Abboud, K. A.; Boncella, J. M. Organometallics 1995, 14, 1567.
11. For recent selected examples, see: (a) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405. (b) Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenziger, N. Organometallics 1989, 8, 2892 and references therein. (c) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (d) Caldarelli, J. L.; Wagner, L. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 2878. (e) Hauptman, E.; Brookhart, M.; Fagan, P. J.; Calabrese, J. C. Organometallics 1994, 13, 774. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137. (g) Vaughan, W. M.; Abboud, K. A.; Boncella, J. M. Organometallics 1995, 14, 1567.
12. For recent selected examples, see: (a) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405. (b) Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenziger, N. Organometallics 1989, 8, 2892 and references therein. (c) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (d) Caldarelli, J. L.; Wagner, L. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 2878. (e) Hauptman, E.; Brookhart, M.; Fagan, P. J.; Calabrese, J. C. Organometallics 1994, 13, 774. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137. (g) Vaughan, W. M.; Abboud, K. A.; Boncella, J. M. Organometallics 1995, 14, 1567.
13. For recent selected examples, see: (a) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405. (b) Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenziger, N. Organometallics 1989, 8, 2892 and references therein. (c) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (d) Caldarelli, J. L.; Wagner, L. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 2878. (e) Hauptman, E.; Brookhart, M.; Fagan, P. J.; Calabrese, J. C. Organometallics 1994, 13, 774. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137. (g) Vaughan, W. M.; Abboud, K. A.; Boncella, J. M. Organometallics 1995, 14, 1567.
14. For recent selected examples, see: (a) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405. (b) Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenziger, N. Organometallics 1989, 8, 2892 and references therein. (c) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (d) Caldarelli, J. L.; Wagner, L. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 2878. (e) Hauptman, E.; Brookhart, M.; Fagan, P. J.; Calabrese, J. C. Organometallics 1994, 13, 774. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137. (g) Vaughan, W. M.; Abboud, K. A.; Boncella, J. M. Organometallics 1995, 14, 1567.
15. For recent selected examples, see: (a) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405. (b) Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenziger, N. Organometallics 1989, 8, 2892 and references therein. (c) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (d) Caldarelli, J. L.; Wagner, L. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 2878. (e) Hauptman, E.; Brookhart, M.; Fagan, P. J.; Calabrese, J. C. Organometallics 1994, 13, 774. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137. (g) Vaughan, W. M.; Abboud, K. A.; Boncella, J. M. Organometallics 1995, 14, 1567.
16. (a) Sünkel, K.; Urban, G.; Beck, W. J. Organomet. Chem. 1985, 290, 231.
17. (b) Appel, M.; Schloter, K.; Heidrich, J.; Beck, W. J. Organomet. Chem. 1987, 322, 77.
18. (c) Fischer, R. A.; Herrmann, W. A. J. Organomet. Chem. 1987, 330, 377.
19. Mahmoud, K. A.; Rest, A. J.; Alt, H. G.; Eichner, M. E.; Jansen, B. M. J. Chem. Soc., Dalton Trans. 1984, 175.
20. Yi, C. S.; Wodka, D. Unpublished results.
21. Brookhart, M.; Grant, B.; Volpe, A. F., Jr. Organometallics 1992, 11, 3920.
22. 4W: C, 43.90; H, 2.79. Found C, 43.87; H, 2.80. mp 122-124°C.
23. 3 groups were rotationally disordered and modeled with occupancy refinement.
24. Song, J.-S.; Szalda, D. J.; Bullock, R. M.; Lawrie, C. J.; Rodkin, M. A.; Norton, J. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1233.
25. See the Supporting Information for detailed experimental procedures and spectral data for complexes 3-5, 7, and 8.
26. (a) Chi, Y.; Hsu, H.-Y.; Peng, S.-M.; Lee, G.-H. J. Chem. Soc., Chem. Commun. 1991, 1019.
27. (b) Bruce, M. I.; Humphrey, M. G.; Matisons, J. G.; Roy, S. K.; Swincer, A. G. Aust. J. Chem. 1984, 37, 1955.
28. (c) Kazlauskas, R. J.; Wrighton, M. S. J. Am. Chem. Soc. 1982, 104, 6005.
29. (d) Kubas, G. J.; Wasserman, H. J.; Ryan, R. R. Organometallics 1985, 4, 2012.
30. 31P} NMR analysis.
31. (a) Atwood, J. D. Inorganic and Organometallic Reaction Mechanisms; Brooks/Cole: Monterey, CA, 1985; Chapter 4 and references therein.
32. (b) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
33. (c) For common examples on the preparation of transition-metal complexes with weakly coordinating ligands, see: Inorg. Synth. 1990, 28, 1.
34. (a) Boutry, O.; Gutiérrez, E.; Monge, A.; Nicasio, M. C.; Pérez, P. J.; Carmona, E. J. Am. Chem. Soc. 1992, 114, 7288.
35. (b) Li, Z-W.; Taube, H. J. Am. Chem. Soc. 1994, 116, 11584.
36. (c) Breen, T. L.; Stephan, D. W. Inorg. Chem. 1992, 31, 4019.
37. (d) Lehmkuhl, H.; Schwickardi, R.; Krüger, C.; Raabe, G. Z. Anorg. Allg. Chem. 1990, 581, 41.
38. (e) Werner, H.; Weber, B.; Nürnberg, O.; Wolf, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1025.
39. (f) Hay-Motherwell, R. S.; Hussain-Bates, B.; Hursthouse, M. B.; Mann, B. E. J. Chem. Soc., Dalton Trans. 1993, 3219.
40. (a) King, R. B.; Iqbal, M. Z.; King, A. D., Jr. J. Organomet. Chem. 1979, 171, 53.
41. (b) Rheingold, A. L.; Harper, J. R. Acta Crystallogr. 1991, C47, 184.
42. (c) Bougeard, P.; Peng, S.; Mlekuz, M.; McGlinchey, M. J. J. Organomet. Chem. 1985, 296, 383.
43. We also observed the formation of a small amount (∼5%) of the dimer 9 in the reaction mixture.