Oxidative carbonylation of alkynyltungsten compounds via protonation with triflic acid

Organometallics

Volumn 17, Issue 13, 1998, Pages 2683-2685

  Liang, Kwei Wen ^a   Chandrasekharam, M ^a   Li, Chien Le ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007005550     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980093h     Document Type: Article

References (35)

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3. Subramanian, L. S.; Garcia, A.; Hanack, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: London, 1995; Vol. 7, p 5143.
4. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
5. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
6. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
7. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
8. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
9. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
10. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
11. For representative reactions, see: (a) Sagl, D.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827. (b) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182. (c) Gassman, P. G.; Singleton, D. A. J. Org. Chem. 1986, 51, 3075. (d) Olah, G. A.; Wu, A. J. Org. Chem. 1991, 56, 2531. (e) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203. (f) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237. (g) Hulin, B.; Koreeda, M. J. Org. Chem. 1984, 49, 207. (h) Childs, R. F.; Shaw, G. S.; Varadarajan, A. S. Synthesis 1982, 198.
12. Review papers: (a) Norton, J. R. In Inorganic Reactions and Methods; Verlag Chemie: Weinheim, Germany, 1987. (b) Pearson, R. G. Chem. Rev. 1985, 85, 41.
13. Review papers: (a) Norton, J. R. In Inorganic Reactions and Methods; Verlag Chemie: Weinheim, Germany, 1987. (b) Pearson, R. G. Chem. Rev. 1985, 85, 41.
14. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Application of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; Chapter 8, p 619.
15. (b) Hegedus, L. S., Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA 1994; Chapter 8, p 433.
16. 2-alkene cations, see the following representative papers: (a) Welker, M. E. Chem. Rev. 1992, 92, 97. (b) Jiang, S.; Turos, E. Organometallics 1993, 12, 4280. (c) Jiang, S.; Turos, E. Tetrahedron Lett. 1991, 4639. (d) Rosenblum, M.; Watkins, J. C. J. Am. Chem. Soc. 1990, 112, 6316.
17. 2-alkene cations, see the following representative papers: (a) Welker, M. E. Chem. Rev. 1992, 92, 97. (b) Jiang, S.; Turos, E. Organometallics 1993, 12, 4280. (c) Jiang, S.; Turos, E. Tetrahedron Lett. 1991, 4639. (d) Rosenblum, M.; Watkins, J. C. J. Am. Chem. Soc. 1990, 112, 6316.
18. 2-alkene cations, see the following representative papers: (a) Welker, M. E. Chem. Rev. 1992, 92, 97. (b) Jiang, S.; Turos, E. Organometallics 1993, 12, 4280. (c) Jiang, S.; Turos, E. Tetrahedron Lett. 1991, 4639. (d) Rosenblum, M.; Watkins, J. C. J. Am. Chem. Soc. 1990, 112, 6316.
19. 2-alkene cations, see the following representative papers: (a) Welker, M. E. Chem. Rev. 1992, 92, 97. (b) Jiang, S.; Turos, E. Organometallics 1993, 12, 4280. (c) Jiang, S.; Turos, E. Tetrahedron Lett. 1991, 4639. (d) Rosenblum, M.; Watkins, J. C. J. Am. Chem. Soc. 1990, 112, 6316.
20. 2-allene cations, see the representative papers: (a) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Blosser, P. W.; Shimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1993, 12, 1393. (d) Chen, C.-C.; Fan, J.-S.; Shieh, S.-J.; Lee, G.-H.; Peng, S.-M.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1996, 118, 9279.
21. 2-allene cations, see the representative papers: (a) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Blosser, P. W.; Shimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1993, 12, 1393. (d) Chen, C.-C.; Fan, J.-S.; Shieh, S.-J.; Lee, G.-H.; Peng, S.-M.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1996, 118, 9279.
22. 2-allene cations, see the representative papers: (a) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Blosser, P. W.; Shimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1993, 12, 1393. (d) Chen, C.-C.; Fan, J.-S.; Shieh, S.-J.; Lee, G.-H.; Peng, S.-M.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1996, 118, 9279.
23. 2-allene cations, see the representative papers: (a) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Blosser, P. W.; Shimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1993, 12, 1393. (d) Chen, C.-C.; Fan, J.-S.; Shieh, S.-J.; Lee, G.-H.; Peng, S.-M.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1996, 118, 9279.
24. 1-vinylidene cations, see the following representative papers: (a) Bruce, M. I. Chem. Rev. 1991, 91, 257. (b) Trost, B. M.; Dyker, G.; Kulawiec, R. J. J. Am. Chem. Soc. 1990, 112, 7809. (c) Trost, B. M.; Martinez, J. A.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402. (d) Trost, B. M.; Flygare, J. A. J. Am. Chem. Soc. 1992, 114, 5467. (e) McDonald, F. E.; Bowman, J. L. Tetrahedron Lett. 1996, 4675.
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