Tungsten η1-five-membered oxygenated heterocycles derived from tungsten η1-propargyl compounds: Systematic syntheses, structural rearrangement, electrophilic alkylations, and oxidative demetalations

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 530-540

  Shu, Hsin Guo ^a   Shiu, Lin Hung ^a   Wang, Shin Hwan ^a   Wang, Sue Lein ^a   Lee, Gene Hsian ^b   Peng, Shie Ming ^b   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0542410392     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9518888     Document Type: Article

References (87)

1. For the application of metal allenyl and propargyl compounds in organic synthesis, see the review paper: (a) Yamamoto, H. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3, p 81. (b) Fleming, I. In Comprehensive Organic Synthesis: Addition to C-X p bonds, Part I; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 2.2, p 575. (c) Panek, J. S. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Chapter 2.5, p 580. (d) Epsztein, R. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam, 1984; Part B, p 107.
2. For the application of metal allenyl and propargyl compounds in organic synthesis, see the review paper: (a) Yamamoto, H. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3, p 81. (b) Fleming, I. In Comprehensive Organic Synthesis: Addition to C-X p bonds, Part I; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 2.2, p 575. (c) Panek, J. S. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Chapter 2.5, p 580. (d) Epsztein, R. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam, 1984; Part B, p 107.
3. For the application of metal allenyl and propargyl compounds in organic synthesis, see the review paper: (a) Yamamoto, H. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3, p 81. (b) Fleming, I. In Comprehensive Organic Synthesis: Addition to C-X p bonds, Part I; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 2.2, p 575. (c) Panek, J. S. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Chapter 2.5, p 580. (d) Epsztein, R. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam, 1984; Part B, p 107.
4. For the application of metal allenyl and propargyl compounds in organic synthesis, see the review paper: (a) Yamamoto, H. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3, p 81. (b) Fleming, I. In Comprehensive Organic Synthesis: Addition to C-X p bonds, Part I; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 2.2, p 575. (c) Panek, J. S. In Comprehensive Organic Synthesis: Addition to C-X p bonds Part II; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Chapter 2.5, p 580. (d) Epsztein, R. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam, 1984; Part B, p 107.
5. For main-group metal allenyl and propargyl compounds, see representative examples: (a) Seyferth, D.; Son, D. Y.; Shah, S. Organometallics 1994, 13, 2105. (b) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (e) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (f) Marshall J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3212. (g) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 50, 6264.
6. For main-group metal allenyl and propargyl compounds, see representative examples: (a) Seyferth, D.; Son, D. Y.; Shah, S. Organometallics 1994, 13, 2105. (b) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (e) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (f) Marshall J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3212. (g) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 50, 6264.
7. For main-group metal allenyl and propargyl compounds, see representative examples: (a) Seyferth, D.; Son, D. Y.; Shah, S. Organometallics 1994, 13, 2105. (b) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (e) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (f) Marshall J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3212. (g) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 50, 6264.
8. For main-group metal allenyl and propargyl compounds, see representative examples: (a) Seyferth, D.; Son, D. Y.; Shah, S. Organometallics 1994, 13, 2105. (b) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (e) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (f) Marshall J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3212. (g) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 50, 6264.
9. For main-group metal allenyl and propargyl compounds, see representative examples: (a) Seyferth, D.; Son, D. Y.; Shah, S. Organometallics 1994, 13, 2105. (b) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (e) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (f) Marshall J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3212. (g) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 50, 6264.
10. For main-group metal allenyl and propargyl compounds, see representative examples: (a) Seyferth, D.; Son, D. Y.; Shah, S. Organometallics 1994, 13, 2105. (b) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (e) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (f) Marshall J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3212. (g) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 50, 6264.
11. For main-group metal allenyl and propargyl compounds, see representative examples: (a) Seyferth, D.; Son, D. Y.; Shah, S. Organometallics 1994, 13, 2105. (b) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (e) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (f) Marshall J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3212. (g) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 50, 6264.
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14. For chemistry of transition-metal propargyl and allenyl compounds, see representative examples: (a) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (b) Raghu, S., Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Pu, J.; Peng, T. S.; Arif, A. M.; Gladysz, J. A. Organometallics 1992, 11, 3232. (d) Blosser, P. W.; Shimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1993, 12, 1393. (e) Benaim, J.; Merour, J.-Y.; Roustan, J. L. C. R. Acad. Sci. Paris, Ser. C 1971, 272, 789.
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16. For chemistry of transition-metal propargyl and allenyl compounds, see representative examples: (a) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (b) Raghu, S., Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Pu, J.; Peng, T. S.; Arif, A. M.; Gladysz, J. A. Organometallics 1992, 11, 3232. (d) Blosser, P. W.; Shimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1993, 12, 1393. (e) Benaim, J.; Merour, J.-Y.; Roustan, J. L. C. R. Acad. Sci. Paris, Ser. C 1971, 272, 789.
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30. Preliminary results of this paper: Wane, S.-H.; Shiu, L.-H.; Shu, H.-G.; Liao, Y.-L.; Wang, S.-L.; Lee, G.-H.; Pena, S.-M.; Liu, R.-S. J. Am. Chem. Soc. 1994, 116, 5967.
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84. 2 as catalyst; see representative examples: (a) Keck, G. E.; Abbott, D. A. Tetrahedron Lett. 1984, 25, 1883. (b) Mikami, K.; Kawamoto, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1359. (c) Hull, C.; Mortlock, S. V.; Thomas, E. J. Tetrahedron 1989, 45, 1007. (d) Koreeda, M.; Tanaka, Y. Chem. Lett. 1982, 1299.
85. 2 as catalyst; see representative examples: (a) Keck, G. E.; Abbott, D. A. Tetrahedron Lett. 1984, 25, 1883. (b) Mikami, K.; Kawamoto, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1359. (c) Hull, C.; Mortlock, S. V.; Thomas, E. J. Tetrahedron 1989, 45, 1007. (d) Koreeda, M.; Tanaka, Y. Chem. Lett. 1982, 1299.
86. 2 as catalyst; see representative examples: (a) Keck, G. E.; Abbott, D. A. Tetrahedron Lett. 1984, 25, 1883. (b) Mikami, K.; Kawamoto, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1359. (c) Hull, C.; Mortlock, S. V.; Thomas, E. J. Tetrahedron 1989, 45, 1007. (d) Koreeda, M.; Tanaka, Y. Chem. Lett. 1982, 1299.
87. 2 as catalyst; see representative examples: (a) Keck, G. E.; Abbott, D. A. Tetrahedron Lett. 1984, 25, 1883. (b) Mikami, K.; Kawamoto, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1359. (c) Hull, C.; Mortlock, S. V.; Thomas, E. J. Tetrahedron 1989, 45, 1007. (d) Koreeda, M.; Tanaka, Y. Chem. Lett. 1982, 1299.