Carbon-carbon bond activation by electrophilic complexes of cobalt: Anomalous [3 + 2 + 2] allyl/alkyne cycloaddition reactions and [5 + 2] cyclopentenyl/alkyne insertion-ring expansion reactions [8]

Journal of the American Chemical Society

Volumn 121, Issue 45, 1999, Pages 10640-10641

  Dzwiniel, Trevor L ^a   Etkin, Nola ^a,b   Stryker, Jeffrey M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF PRINCE EDWARD ISLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBON; COBALT;

CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033579108     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992598k     Document Type: Letter

References (37)

1. Reviews: Herrmann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. Crabtree, R. H. Chem. Rev. 1985, 85, 245.
2. Reviews: Herrmann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048. Crabtree, R. H. Chem. Rev. 1985, 85, 245.
3. Additional references are provided in the Supporting Information.
4. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
5. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
6. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
7. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
8. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
9. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
10. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
11. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
12. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
13. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
14. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
15. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
16. Lanthanide/early transition metals: (a) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51. (b) Bercaw, J. E. Pure Appl. Chem. 1990, 62, 1151. Burger, B. J.; Thompson, M.; Cotter, D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566. (c) Horton, A. D. Organometallics 1996, 15, 2675. Etienne, M.; Mathieu, R.; Donnadieu, B. J. Am. Chem. Soc. 1997, 119, 3218. (d) Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362. (e) Mise, T.; Kageyama, A.; Miya, S.; Yamazaki, H. Chem. Lett. 1991, 1525. (f) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025. (g) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565. (h) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424. (i) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (j) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147. (k) Yang, X.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392 and references therein.
17. Electrophilic late metal examples: (a) Terheijden, J.; van Koten, G.; Vinke, I. C.; Spek, A. L. J. Am. Chem. Soc. 1985, 107, 2891. (b) Nicholls, J. C.; Spencer, J. L. Organometallics 1994, 13, 1781. Cracknell, R. B.; Nicholls, J. C.; Spencer, J. L. Organometallics 1996, 15, 446.
18. Electrophilic late metal examples: (a) Terheijden, J.; van Koten, G.; Vinke, I. C.; Spek, A. L. J. Am. Chem. Soc. 1985, 107, 2891. (b) Nicholls, J. C.; Spencer, J. L. Organometallics 1994, 13, 1781. Cracknell, R. B.; Nicholls, J. C.; Spencer, J. L. Organometallics 1996, 15, 446.
19. Electrophilic late metal examples: (a) Terheijden, J.; van Koten, G.; Vinke, I. C.; Spek, A. L. J. Am. Chem. Soc. 1985, 107, 2891. (b) Nicholls, J. C.; Spencer, J. L. Organometallics 1994, 13, 1781. Cracknell, R. B.; Nicholls, J. C.; Spencer, J. L. Organometallics 1996, 15, 446.
20. (a) Etkin, N.; Dzwiniel, T. L.; Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1998, 120, 9702.
21. (b) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995,117, 8275.
22. 6
23. Experimental details and complete spectroscopic and analytical data are provided as Supporting Information.
24. Both complexes 2 and 6 are obtained from reactions conducted in either dichloromethane or trifluoroethanol; Scheme 2 reports optimal procedures.
25. 8
26. 8
27. 13
28. (a) Lutsenko, Z. L.; Aleksandrov, G. G.; Petrovskii, P. V.; Shubina, E. S.; Andrianov, V. G.; Struchkov, Yu. T.; Rubezhov, A. Z. J. Organomet. Chem. 1985, 281, 349. Lutsenko, Z. L.; Petrovskii, P. V.; Bezrukova, A. A.; Rubezhov, A. Z. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 735. (b) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 12, 600. (c) Nehl, H. Chem. Ber. 1993, 126, 1519. (d) Older, C. M.; Stryker, I. M. Organometallics 1998, 17, 5596.
29. (a) Lutsenko, Z. L.; Aleksandrov, G. G.; Petrovskii, P. V.; Shubina, E. S.; Andrianov, V. G.; Struchkov, Yu. T.; Rubezhov, A. Z. J. Organomet. Chem. 1985, 281, 349. Lutsenko, Z. L.; Petrovskii, P. V.; Bezrukova, A. A.; Rubezhov, A. Z. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 735. (b) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 12, 600. (c) Nehl, H. Chem. Ber. 1993, 126, 1519. (d) Older, C. M.; Stryker, I. M. Organometallics 1998, 17, 5596.
30. (a) Lutsenko, Z. L.; Aleksandrov, G. G.; Petrovskii, P. V.; Shubina, E. S.; Andrianov, V. G.; Struchkov, Yu. T.; Rubezhov, A. Z. J. Organomet. Chem. 1985, 281, 349. Lutsenko, Z. L.; Petrovskii, P. V.; Bezrukova, A. A.; Rubezhov, A. Z. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 735. (b) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 12, 600. (c) Nehl, H. Chem. Ber. 1993, 126, 1519. (d) Older, C. M.; Stryker, I. M. Organometallics 1998, 17, 5596.
31. (a) Lutsenko, Z. L.; Aleksandrov, G. G.; Petrovskii, P. V.; Shubina, E. S.; Andrianov, V. G.; Struchkov, Yu. T.; Rubezhov, A. Z. J. Organomet. Chem. 1985, 281, 349. Lutsenko, Z. L.; Petrovskii, P. V.; Bezrukova, A. A.; Rubezhov, A. Z. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 735. (b) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 12, 600. (c) Nehl, H. Chem. Ber. 1993, 126, 1519. (d) Older, C. M.; Stryker, I. M. Organometallics 1998, 17, 5596.
32. (a) Lutsenko, Z. L.; Aleksandrov, G. G.; Petrovskii, P. V.; Shubina, E. S.; Andrianov, V. G.; Struchkov, Yu. T.; Rubezhov, A. Z. J. Organomet. Chem. 1985, 281, 349. Lutsenko, Z. L.; Petrovskii, P. V.; Bezrukova, A. A.; Rubezhov, A. Z. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 735. (b) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 12, 600. (c) Nehl, H. Chem. Ber. 1993, 126, 1519. (d) Older, C. M.; Stryker, I. M. Organometallics 1998, 17, 5596.
33. 8 to 14 proceeds in low yield regardless of conditions.
34. 6a,13c
35. 5-pentadienyl products are observed in the present system, even under conditions of alkyne deficiency.
36. 5b
37. Alkyl/alkylidene 1,2-migration: Casty, G. L.; Stryker, J. M. Organometallics 1997, 16, 3083 and references therein.