Syntheses, structures, and thermolyses of pentacoordinate 1,2-oxastibetanes: Potential intermediates in the reactions of stibonium ylides with carbonyl compounds

Journal of Organic Chemistry

Volumn 71, Issue 2, 2006, Pages 659-670

  Uchiyama, Yosuke ^a   Kano, Naokazu ^a   Kawashima, Takayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMONY; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; OLEFINS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; X RAY CRYSTALLOGRAPHY;

BIPYRAMIDAL STRUCTURE; CARBONYL COMPOUNDS; POLAR TRANSITION STATE; THERMOLYSES;

PARAFFINS;

1,2 OXASTIBETANE DERIVATIVE; ALKENE; ANTIMONY; ANTIMONY DERIVATIVE; BORANE DERIVATIVE; CARBONYL DERIVATIVE; ETHYLENE OXIDE; STIBONIUM YLIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DECOMPOSITION; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 30744468853     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0520700     Document Type: Article

References (48)

1. (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
2. (b) Edmonds, M.; Abell, A. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, Germany, 2004; pp 1-17.
3. Lloyd, D.; Gosney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45.
4. (a) Chen, C.; Huang, Y.-Z.; Shen, Y.; Liao, Y. Heteroat. Chem. 1990, 1, 49.
5. (b) Liao, Y.; Huang, Y.-Z.; Zhang, L.-J.; Chen, C. J. Chem. Res. (S) 1990, 388.
6. (c) Matano, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2703.
7. Huang, Y.-Z.; Liao, Y.; Chen, C. J. Chem. Soc., Chem. Commun. 1990, 85.
8. Henry, M. C.; Wittig, G. J. Am. Chem. Soc. 1960, 52, 563.
9. (a) Vedejs, E.; Snoble, K. A. J. J. Am. Chem. Soc. 1973, 95, 5778.
10. (b) Vedejs, E.; Meier, G. P.; Snoble, K. A. J. J. Am. Chem. Soc. 1981, 103, 2823.
11. Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080.
12. (a) Johnson, A. W.; LaCount, R. B. J. Am. Chem. Soc. 1961, 83, 417.
13. (b) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782.
14. (c) Aubé, J. In Comprehensive Organic Synthesis: Selectivity, Strategy, and Efficiency in Modern Synthetic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; pp 819-842.
15. (a) Ohno, F.; Kawashima, T.; Okazaki, R. J. Am. Chem. Soc. 1996, 118, 697.
16. (b) Kawashima, T.; Ohno, F.; Okazaki, R.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 1996, 118, 12455.
17. (c) Ohno, F.; Kawashima, T.; Okazaki, R. Chem. Commun. 1997, 1671.
18. (d) Ohno, F.; Kawashima, T.; Okazaki, R. Chem. Commun. 2001, 463.
19. (e) Kano, N.; Takahashi, T.; Kawashima, T, Tetrahedron Lett. 2002, 43, 6775.
20. Ramirez, F.; Smith, C. P.; Pilot, J. F. J. Am. Chem. Soc. 1968, 90, 6726.
21. Vedejs, E.; Marth, C. Tetrahedron Lett. 1987, 28, 3445.
22. (a) Kawashima, T.; Kato, K.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 4008.
23. (b) Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869.
24. Perozzi, E. F.; Michalak, R. S.; Figuly, G. D.; Stevenson, W. H., III; Dess, D. B.; Ross, M. R.; Martin, J. C. J. Org. Chem. 1981, 46, 1049.
25. Uchiyama, Y.; Kano, N.; Kawashima, T. J. Am. Chem. Soc. 2003, 125, 13346.
26. (a) Akiba, K.-y.; Fujikawa, H.; Sunaguchi, Y.; Yamamoto, Y. J. Am. Chem. Soc. 1987, 109, 1245.
27. (b) Yamamoto, Y.; Fujikawa, H.; Fujishima, H.; Akiba, K.-y. J. Am. Chem. Soc. 1989, 111, 2276.
28. Hiiro, T.; Atarashi, Y.; Kambe, N.; Fujiwara, S.; Oguwa, A.; Ryu, I.; Sonoda, N. Organometallics 1990, 9, 1355.
29. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1875.
30. Emsley, J. In The Elements, 3rd ed.; Oxford University Press: New York, 1998; pp 22-23, 152-153.
31. Kawashima, T.; Soda, T.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1096,
32. Kojima, S.; Sugino, M.; Matsukawa, S.; Nakamoto, M.; Akiba, K.-y. J. Am. Chem. Soc. 2002, 124, 7674.
33. Kawashima, T.; Nishiwaki, Y.; Okazaki, R. J. Orgcmomet. Chem. 1995, 499, 143.
34. (a) Yamamoto, Y.; Akiba, K.-y. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley: New York, 1998; Chapter 9, pp 279-294.
35. (b) Akiba, K.-y. Pure Appl. Chem. 1996, 68, 837.
36. Moc, J.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 11790.
37. Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970.
38. (a) Matsukawa, S.; Kojima, S.; Kajiyama, K.; Yamamoto, Y.; Akiba, K.-y.; Re, S.; Nagase, S. J. Am. Chem. Soc. 2002, 124, 13154.
39. (b) Kawashima, T.; Watanabe, K.; Okazaki, R. Tetrahedron Lett. 1997, 38, 551.
40. (c) Kojima, S.; Akiba, K.-y. Tetrahedron Lett. 1997, 38, 547.
41. (d) Kojima, S.; Kawaguchi, K.; Akiba, K.-y. Tetrahedron Lett. 1997, 38, 7753.
42. (e) Bojin, M. L.; Barkallah, S.; Evans, S. A., Jr. J. Am. Chem. Soc. 1996, 118, 1549.
43. Marvel, C. S.; Johnston, H. W.; Meier, J. W.; Mastin, T. W.; Whitson, J.; Himel, C. M. J. Am. Chem. Soc. 1944, 66, 914.
44. The yields of 7a, 8, and 9 were calculated assuming that 1 mol of 6 gives 1 mol of 7a and 8, and 0.5 mol of 9, respectively.
45. Shanklin, J. R.; Johnson, C. R.; Ollinger, J.; Coates, R. M. J. Am. Chem. Soc. 1973, 95, 3429.
46. Nader, B. S.; Cordova, J. A.; Reese, K. E.; Powell, C. L. J. Org. Chem. 1994, 50, 2898.
47. House, H. O. J. Am. Chem. Soc. 1955, 77, 3070.
48. The yields of 30, 34, and 35 were calculated assuming that 1 mol of 7c given 1 mol of 30 and 34, and 0.5 mol of 35, respectively.