Destiny of transient phosphenium ions generated from the addition of electrophiles to phosphaalkenes: Intramolecular C-H activation, donor-acceptor formation, and linear oligomerization

Organometallics

Volumn 23, Issue 25, 2004, Pages 5913-5923

  Tsang, Chi Wing ^a   Rohrick, Crystal A ^a   Saini, Tejindra S ^a   Patrick, Brian O ^a   Gates, Derek P ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANIONIC POLYMERIZATION; CATIONIC POLYMERIZATION; CHEMICAL ACTIVATION; CHEMICAL BONDS; OLEFINS; OLIGOMERS; SOLUTIONS;

OLIGOMERIZATION; PHOPHAALKENES; POLYMERIZATION INITIATORS; REACTIVE CARBOCATION;

COMPLEXATION;

EID: 10444237388     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0495022     Document Type: Article

References (105)

1. Power, P. P. Chem. Rev. 1999, 99, 3463.
2. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
3. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
4. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
5. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
6. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
7. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
8. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
9. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
10. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
11. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
12. For reviews on phosphaalkenes, see: (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998. (c) Weber, L. Eur. J. Inorg. Chem. 2000, 2425. (d) Yoshifuji, M. J. Chem. Soc., Dalton Trans. 1998, 3343. (e) Weber, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 271. (f) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413. (g) Mathey, F. Acc. Chem. Res. 1992, 25, 90. (h) Appel, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990. (i) Appel, R.; Knoll, F. Adv. Inorg. Chem. 1989, 33, 259. (j) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 924. (k) Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
13. Wright, V. A.; Gates, D. P. Angew. Chem., Int. Ed. 2002, 41, 2389.
14. Smith, R. C.; Chen, X.; Protasiewicz, J. D. Inorg. Chem. 2003, 42, 5468.
15. Tsang, C.-W.; Yam, M.; Gates, D. P. J. Am. Chem. Soc. 2003, 125, 1480.
16. Gillon, B. H.; Gates, D. P. Chem. Commun. 2004, 1868.
17. The electronic structure of phosphaalkenes has been studied extensively using photoelectron spectroscopy and molecular modeling. The two filled frontier orbitals (the lone pair on phosphorus and the (2p-3p)π bond) are closely spaced in energy, and the order is highly dependent on the nature of the substituants. (See, for example: Lacombe, S.; Gonbeau, D.; Cabioch, J.-L; Pellerin, B.; Denis, J.-M.; Pfister-Guillouzo, G. J. Am. Chem. Soc. 1988, 110, 6964 and references therein).
18. Nixon, J. F. Chem. Rev. 1988, 88, 1327.
19. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
20. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
21. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
22. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
23. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
24. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
25. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
26. Most studies of the coordination chemistry of phosphaalkenes have involved transition metals. Selected recent examples: Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935. Weber, L.; Dembeck, G.; Lönneke, P.; Stammler, H.; Neumann, B. Organometallics 2001, 20, 2288. Bridgeman, A. J.; Mays, M. J.; Woods, A. D. Organometallics 2001, 20, 2076. Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512. van der Sluis, M.; Beverwijk, V.; Termaten, A.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Organometallics 1999, 18, 1402. Benvenutti, M. H. A.; Cenac, N.; Nixon, J. F. Chem. Commun. 1997, 1327. Hobbold, M.; Streubel, R.; Benvenutti, M. H. A.; Hitchcock, P. B.; Nixon, J. F. Organometallics 1997, 16, 3726. Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
27. -. This is true for the σ-system; however, evidence from UV and magnetic circular dichroism of phosphinines suggests that the effective π-electronegativity of P is similar to or higher than that of C. For a useful discussion of this see: Waluk, J.; Klein, H.-P.; Ashe, A. J., III; Michl, J. Organometallics 1989, 8, 2804.
28. Niecke, E.; Symalla, E. Chimia 1985, 39, 320.
29. Gudat, D.; Niecke, E.; Krebs, B.; Dartmann, M. Chimia 1985, 39 277
30. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Am. Chem. Soc. 1983, 105, 4845.
31. Loss, S.; Widauer, C.; Grützmaoher, H. Angew. Chem., Int. Ed. 1999, 38, 3329.
32. For reviews, see: (a) Cowley, A. H.; Kemp, R. A. Chem. Rev. 1985, 85, 367. (b) Sanchez, M.; Mazières, M.-R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990; p 129. (c) Driess, M.; Grützmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828.
33. For reviews, see: (a) Cowley, A. H.; Kemp, R. A. Chem. Rev. 1985, 85, 367. (b) Sanchez, M.; Mazières, M.-R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990; p 129. (c) Driess, M.; Grützmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828.
34. For reviews, see: (a) Cowley, A. H.; Kemp, R. A. Chem. Rev. 1985, 85, 367. (b) Sanchez, M.; Mazières, M.-R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990; p 129. (c) Driess, M.; Grützmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828.
35. Burford, N.; Ragogna, P. J. Dalton 2002, 4307.
36. Gudat, D. Coord. Chem. Rev. 1997, 163, 71.
37. Reed, R. W.; Xie, Z.; Reed, C. A. Organometallics 1995, 14, 5002.
38. Dumitrescu, A.; Gornitzka, H.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Eur. J. Inorg. Chem. 2002, 1953.
39. +; cf. Chart 1, type I) are stable and exhibit reactivity much different from that of phosphenium ions. See, for example: Moores, A.; Ricard, L.; Le Floch, P. Angew. Chem., Int. Ed. 2003, 42, 4940.
40. 4, has been detected spectroscopically; however, its high reactivity results in C-H activation of Cp*. See: Cowley, A. H.; Mehrota, S. K. J. Am. Chem. Soc. 1983, 105, 2074. See also ref 12.
41. Tsang, C.-W.; Rohrick, C. A.; Saini, T. S.; Patrick, B. O.; Gates, D. P. Organometallics 2002, 21, 1008.
42. Mundt, O.; Becker, G.; Uhl, W. Z. Anorg. Allg. Chem. 1986, 540/541, 319.
43. Appel, R.; Casser, C.; Immenkeppel, M.; Knoch, F. Angew. Chem., Int. Ed. Engl. 1984, 23, 895.
44. (a) Appel, R.; Casser, C.; Knoch, F. J. Organomet. Chem. 1985, 293, 213.
45. (b) Etemad-Moghadam, G.; Rifqui, M.; Layrolle, P.; Berlan, J.; Koenig, M. Tetrahedron Lett. 1991, 32, 5965.
46. (c) Breen, T. L.; Stephan, D. W. J. Am. Chem. Soc. 1995, 117, 11914.
47. (d) Ito, S.; Yoshifuji, M. Chem. Lett. 1998, 651.
48. (e) Termaten, A. T.; Nijbacker, T.; Schakel, M.; Lutz, M.; Spek, A. L.; Lammertsma, K. Organometallics 2002, 21, 3196.
49. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
50. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
51. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
52. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
53. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
54. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
55. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
56. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
57. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
58. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
59. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
60. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
61. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
62. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
63. See, for example: Ito, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 1998, 553, 135. van der Sluis, M.; Klootwjjk, A.; Wit, J. B. M.; Bickelhaupt, F.; Veldman, N.; Spek, A. L.; Jolly, P. W. J. Organomet. Chem. 1997, 529, 107. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Commun. 1997, 1637. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555. Yoshifuji, M.; Ito, S.; Toyata, K.; Yasunami, M. Bull. Chem. Soc. Jpn. 1995, 68, 1206. Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747. Jun, H.; Angelici, R. J. Organometallics 1994, 13, 2454. Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163. Goede, S. J.; van Schalk, H. P.; Bickelhaupt, F. Organometallics 1992, 11, 3844. Goede, S. J. ; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677. Jun, H.; Young, V. G., Jr.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 9379. Yoshifuji, M.; Toyota, K.; Yoshimura, H. Chem. Lett. 1991, 491. Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733. Markl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360. Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
64. van der Knaap, T. A.; Klebach, T. C.; Visser, F.; Bickelhaupt, F.; Ros, P.; Baerends, E. J.; Stam, C. H.; Konijn, M. Tetrahedron 1984, 40, 765.
65. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
66. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
67. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
68. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
69. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
70. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
71. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
72. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
73. See for example: Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2001, 123, 6925. Straddiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958. Cowley, A. H.; Gabbaï, P.; Schluter, R.; Atwood, D. J. Am. Chem. Soc. 1992, 114, 3142. Gouygou, M.; Tachon, C.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1989, 30, 7411. Yoshifuji, M. ; Sato, T.; Inamoto, N. Chem. Lett. 1988, 1735. Karsch, H. H.; Reisacher, H.-U. ; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 454. Cowley, A. H.; Kilduff, J. E.; Norman, N. C.; Pakulski, M. J. Chem. Soc. Dalton Trans. 1986, 1801. Cowley, A. H.; Pakulski, M. K. J. Am. Chem. Soc. 1984, 106, 1491.
74. Beagley, B.; Schmidling, D. G.; Steer, I. A. J. Mol Struct. 1974, 21, 437.
75. Golubinskaya, L. M.; Golubinskii, A. V.; Mastryukov, V. S.; Vilkov, L. V.; Bregadze, V. I. J. Organomet. Chem. 1978, 117, C4.
76. +-bridged [1]diphosphaferrocenophane has been structurally characterized. See, for example: Sava, X.; Melaimi, M.; Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. New J. Chem. 2002, 26, 1378.
77. 3· THF. See: Yoshifuji, M.; Takahashi, H.; Toyota, K. Heteroat. Chem. 1999, 10, 187.
78. van der Knaap, T. A.; Bickelhaupt, F.; Kraaykamp, J. G.; van Koten, G.; Bernards, J. P. C.; Edzes, H. T.; Veeman, W. S.; de Boer, E.; Baerends, E. J. Organometallics 1984, 3, 1804.
79. Cowley, A. H.; Jones, R. A.; Lasch, J. G.; Norman, N. C.; Stewart, C. A. ; Stuart, A. L.; Atwood, J. L.; Hunter, W. E.; Zhang, H.-M. J. Am. Chem. Soc. 1984, 106, 7015.
80. Al-Resayes, S. I.; Klein, S. I.; Kroto, H. W.; Meidine, M. F.; Nixon, J. F. J. Chem. Soc., Chem. Commun. 1983, 930.
81. Gudat, D.; Nieger, M.; Schmitz, K.; Szarvas, L. Chem. Commun. 2002, 1820.
82. van der Knaap, T. A.; Bickelhaupt, F.; van der Poel, H.; van Koten, G.; Stam, C. H. J. Am. Chem. Soc. 1982, 104, 1756.
83. van der Knaap, T. A.; Jenneskens, L. W.; Meeuwissen, H. J.; Bickelhaupt, F.; Walther, D.; Dinjus, E.; Uhlig, E.; Spek, A. L. J. Organomet. Chem. 1983, 254, C33.
84. Schmidbaur, H.; Reber, G.; Schier, A.; Wagner, F.; Müller, G. Inorg. Chim. Acta 1988, 147, 143.
85. Nickel, T.; Goddard, R.; Krüger, C.; Pörschke, K.-R. Angew. Chem., Int. Ed. Engl. 1994, 33, 879.
86. Wolf, J.; Manger, M.; Schmidt, U.; Fries, G.; Barth, D.; Weberndorfer, B.; Vicic, D. A.; Jones, W. D.; Werner, H. J. Chem. Soc., Dalton Trans. 1999, 1867.
87. 3 has been reported to give cyclic dimeric and trimeric species. See: Burford, N.; Cameron, T. S.; Conroy, K. D.; Ellis, B.; Lumsden, M.; Macdonald, C. L. B.; McDonald, R.; Phillips, A. D.; Ragogna, P. J.; Schurko, R. W.; Walsh, D.; Wasylishen, R. E. J. Am. Chem. Soc. 2002, 124, 14012.
88. Odian, G. Principles of Polymerization; Wiley: New York, 1991.
89. Burford, N.; Cameron, T. S.; Ragogna, P. J.; Ocando-Mavarez, E.; Gee, M. ; McDonald, R.; Wasylishen, R. E. J. Am. Chem. Soc. 2001, 123, 7947
90. Abrams, M. B.; Scott, B. L.; Baker, R. T. Organometallics 2000, 19, 4944.
91. Schultz, C. W.; Parry, R. W. Inorg. Chem. 1976, 15, 3046.
92. Loss, S.; Widauer, C.; Rüegger, H.; Fleischer, U.; Marchand, C. M.; Grützmacher, H.; Frenking, G. Dalton 2003, 85.
93. Matyjaszewski, K., Ed. Controlled Radical Polymerization; ACS Symposium Series 685; American Chemical Society: Washington, DC, 1998.
94. Bourissou, D.; Bertrand, G. Top. Curr. Chem. 2002, 220, 1.
95. Mathey, F. Chem. Rev. 1990, 90, 997.
96. Kato, T.; Gornitzka, H.; Baceiredo, A.; Schoeller, W. W.; Bertrand, G. Science 2000, 289, 754.
97. Gudat, D.; Nieger, M.; Niecke, E. J. Chem. Soc., Dalton Trans. 1989, 693.
98. Roques, C.; Mazieres, M.-R.; Majorai, J.-P.; Sanchez, M. Tetrahedron Lett. 1988, 29, 4547.
99. Brasch, N. E.; Hamilton, I. G.; Krenske, E. H.; Wild, S. B. Organometallics 2004, 23, 299.
100. Cowley, A. H.; Kemp, R. A.; Wilburn, J. C. Inorg. Chem. 1981, 20, 4289.
101. Pangborn, A:B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
102. Cowley, A. H.; Norman, N. C.; Pakulski, M. In Inorganic Synthesis; Ginsberg, A. P., Ed.; Wiley: New York; Vol. 27, p 235.
103. Becker, G.; Uhl, W.; Wessely, H.-J. Z. Anorg. Allg. Chem. 1981, 479, 41.
104. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Oxford, U.K., 1996. To dry KOH we follow the procedure for drying NaOH on p 429.
105. 3).