Formation of difluoromethylene-arenium complexes by consecutive Aryl- CF3 C-C bond activation and C-F bond cleavage

Journal of the American Chemical Society

Volumn 121, Issue 28, 1999, Pages 6652-6656

  Van Der Boom, Milko E ^a   Ben David, Yehoshoa ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; COMPLEX FORMATION; COVALENT BOND; REACTION ANALYSIS; SYNTHESIS; THERMOSTABILITY;

EID: 0033591913     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990779g     Document Type: Article

References (75)

1. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
2. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
3. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
4. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
5. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
6. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
7. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
8. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
9. For some reviews regarding bond activation see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. (c) Saunders, G. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2615. (d) Burdeniuc, J.; Jedlicak, B.; Crabtree, R. H. Chem. Ber./Recueil 1997, 130, 145. (e) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 373. (f) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759. (g) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (h) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180. (i) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870.
10. (a) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779.
11. (b) Nicholls, J. C.; Spencer, J. L. Organometallics 1994, 13, 1781.
12. (c) For a recent theoretical study on C-C bond activation see: Holthausen, M. C.; Koch, W. J. Am. Chem. Soc. 1996, 118, 9932.
13. (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699.
14. (b) Gozin, M.; Aizenberg, M.; Liou, S.-Y.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1994, 370, 42.
15. (c) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774.
16. (d) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965.
17. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167.
18. (f) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406.
19. (g) Gandelman, M.; Vigalok, A.; Shimon, L. J. W.; Milstein, D. Organometallics 1997, 16, 3981.
20. (h) Liou, S.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687.
21. (i) van der Boom, M. E.; Ben-David, Y.; Milstein, D. Chem. Commun. 1998, 917.
22. (j) van der Boom, M. E.; Liou, S.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
23. (k) Rybtchinski, B.; Milstein, D. J. Am. Chem. Soc. 1999, 127, 4528.
24. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
25. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
26. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
27. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
28. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
29. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
30. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
31. For some examples of intermolecular C-F activation by platinum metals see: (a) Whittlesy, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187. (b) Edelbach, B. L.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734. (c) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659. (d) Hughes, R. P.; Linder, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (e) Lopez, O.; Crespo, M.; Font-Bardia, M.; Solans, X. Organometallics 1997, 16, 1233. (f) Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582. (g) Hintermann, S.; Pregosin, P. S.; Ruegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225. (h) For a recent theoretical study on C-F bond activation see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 10178.
32. (a) Blum, O.; Frolow, F.; Milstein, D. J. Chem. Soc., Chem. Commun. 1991, 258.
33. (b) Aizenberg, M.; Milstein, D. Science 1994, 265, 359.
34. (c) Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 8674.
35. (a) van der Boom, M. E.; Liou, S.-Y.; Ben-David, Y.; Vigalok, A.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 625.
36. (b) van der Boom, M. E.; Liou, S.-Y.; Ben-David, Y.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 6531.
37. Taylor, R. Electrophilic Aromatic Substitution; John Wiley & Sons: New York, 1990.
38. (a) van Koten, G.; Timmer, K.; Noltes, J. G.; Spek, A. L. J. Chem. Soc., Chem. Commun. 1978, 250.
39. (b) Grove, D. M.; van Koten, G.; Louwen, J. N.; Noltes, J. G.; Spek, A. L.; Ubbels, H. J. C. J. Am. Chem. Soc. 1982, 104, 6609.
40. (c) Grove, D. M.; van Koten, G.; Ubbels, H. J. C. Organometallics 1982, 1, 1366.
41. (d) Terheijden, J.; van Koten, G.; Vinke, I. C.; Spek, A. L. J. Am. Chem. Soc. 1985, 107, 2891.
42. (e) Steenwinkel, P.; Kooijman, H.; Smeets, W. J. J.; Spek, A. L.; Grove, D. M.; van Koten, G. Organometallics 1998, 17, 5411.
43. 4] see: Ortiz, J. V.; Havlas, Z.; Hoffmann, R. Helv. Chim. Acta 1984, 67, 1.
44. (a) Vigalok, A.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 7873.
45. (b) Vigalok, A.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 477.
46. (c) Vigalok, A.; Rybtchinski, B.; Ben-David, Y.; Shimon, L. J. W.; Milstein, D. Organometallics 1999, 18, 895.
47. 2) was very recently structurally characterized. Lee, D. W.; Kaska, W. C.; Jensen, C. M. Organometallics 1998, 17, 1.
48. (b) Nemeh, S.; Jensen, C.; Binamira-Soriaga, E.; Kaska, W. C. Organometallics 1983, 2, 1442.
49. (c) Moulton, C. J.; Shaw, B. L. J. Chem. Soc. 1976, 1020.
50. For a report on C-F versus C-C bond activation with lanthanide cations in the gas phase see: Schwarz, H.; Hornung, G.; Cornehl, H. H. J. Am. Chem. Soc. 1996, 118, 9960.
51. (a) Kaplan, A. W.; Bergman, R. G. Organometallics 1997, 16, 1106.
52. (b) Kaplan, A. W.; Bergman, R. G. Organometallics 1998, 17, 5072.
53. + species have been studied by Olah et al.: Olah, G. A.; Mo, Y. K. J. Org. Chem. 1973, 38, 2686.
54. + species see: Ferraris, D.; Cox, C.; Anand, R.; Lectka, T. J. Am. Chem. Soc. 1997, 119, 4319.
55. Arene carbonium ions generated in acidic media exhibit similar spectroscopic properties; cyclohexadienyl cations exhibit an absorption band in the UV/vis spectrum at λ ∼ 400 nm. Brouwer, D. M.; Mack, E. L.; Maclean, L. In Carbonium Ions; Olah, G. A., Scheyer, P. V., Eds.; Wiley- Interscience: New York, 1970; Vol. 11
56. (a) King, R. B. Acc. Chem. Res. 1970, 3, 417.
57. (b) Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411.
58. (a) For a review on formation and reactivity of transition-metal dihalocarbene complexes see: Brothers, J. P.; Roper, W. R. Chem. Rev. 1988, 88, 1293.
59. (b) Anderson, S.; Hill, A. F.; Clark, G. R. Organometallics 1992, 11, 1988.
60. (c) Michelin, R. A.; Ros, R.; Guadalupi, G.; Bombieri, G.; Benetollo, F.; Chapuis, G. Inorg, Chem. 1989, 28, 840.
61. (d) Burch, R. R.; Calabrese, J. C.; Ittel, S. D. Organometallics 1988, 7, 1642.
62. (e) Richmond, T. G.; Shriver, D. F. Organometallics 1983, 2, 1061.
63. (f) Richmond, T. G.; Shriver, D. F. Organometallics 1984, 3, 305.
64. (g) Richmond, T. G.; Crespi, A. M.; Shriver, D. F. Organometallics 1984, 3, 314.
65. (h) Reger, D. L.; Dukes, M. D. J. Organomet. Chem. 1978, 153, 67.
66. (i) Clark, B. R.; Hoskins, S. V.; Roper, W. R. J. Organomet. Chem. 1982, 234, C9.
67. (a) Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1992, 114, 7085.
68. (b) Milstein, D. Unpublished results.
69. (a) Jia, G.; Lee, H. M.; Xia, H. P.; Williams, I. D. Organometallics 1996, 15, 5453.
70. (b) Lee, H. M.; Yao, J.; Jia, G. Organometallics 1997, 16, 3927.
71. Dani, P.; Karlen, T.; Gossage, R. A.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1997, 119, 11317.
72. 2 species by α C-F migration see: Huang, D.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 3185.
73. 1e,16 Handbook of Chemistry and Physics, 57th ed.; CRC Press: Boca Raton, FL, 1976-1977.
74. van der Ent, A.; Onderdelinden, A. L. Inorg. Synth. 1973, 14, 92.
75. Carr, G. E.; Chambers, R. D.; Holmes, T. F.; Parker, D. G. J. Chem. Soc., Perkin Trans, 1 1988, 921.