Synthesis, crystal structure, and thermolysis of a pentacoordinate 1,2λ6-oxathietane: An intermediate of the Corey-Chaykovsky reaction of oxosulfonium ylides?

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 697-698

  Ohno, Fumihiko ^a   Kawashima, Takayuki ^a   Okazaki, Renji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000514151     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953533u     Document Type: Article

References (27)

1. For the Wittig reactions, see: (a) Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, pp 1316-1329. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. For the Peterson reactions, see: (c) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; pp 58-73. (d) Ager, D. J. Org. React. (N.Y.) 1990, 38, 1-223. For the Peterson-type reactions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410-429. (f) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; pp 176-177.
2. For the Wittig reactions, see: (a) Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, pp 1316-1329. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. For the Peterson reactions, see: (c) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; pp 58-73. (d) Ager, D. J. Org. React. (N.Y.) 1990, 38, 1-223. For the Peterson-type reactions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410-429. (f) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; pp 176-177.
3. For the Wittig reactions, see: (a) Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, pp 1316-1329. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. For the Peterson reactions, see: (c) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; pp 58-73. (d) Ager, D. J. Org. React. (N.Y.) 1990, 38, 1-223. For the Peterson-type reactions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410-429. (f) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; pp 176-177.
4. For the Wittig reactions, see: (a) Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, pp 1316-1329. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. For the Peterson reactions, see: (c) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; pp 58-73. (d) Ager, D. J. Org. React. (N.Y.) 1990, 38, 1-223. For the Peterson-type reactions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410-429. (f) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; pp 176-177.
5. For the Wittig reactions, see: (a) Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, pp 1316-1329. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. For the Peterson reactions, see: (c) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; pp 58-73. (d) Ager, D. J. Org. React. (N.Y.) 1990, 38, 1-223. For the Peterson-type reactions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410-429. (f) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; pp 176-177.
6. For the Wittig reactions, see: (a) Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, pp 1316-1329. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. For the Peterson reactions, see: (c) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; pp 58-73. (d) Ager, D. J. Org. React. (N.Y.) 1990, 38, 1-223. For the Peterson-type reactions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410-429. (f) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; pp 176-177.
7. (a) Kawashima, T.; Kato, K.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 4008-4110. Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869-870.
8. (a) Kawashima, T.; Kato, K.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 4008-4110. Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869-870.
9. (b) Kawashima, T.; Takami, H.; Okazaki, R. J. Am. Chem. Soc. 1994, 116, 4509-4510.
10. (c) Kawashima, T.; Iwama, N.; Okazaki, R. Ibid. 1992, 114, 7598-7599.
11. (d) Kawashima, T.; Nishiwaki, Y.; Okazaki, R. J. Organomet. Chem. 1995, 499, 143-146.
12. (e) Kawashima, T.; Iwama, N.; Okazaki, R. J. Am. Chem. Soc. 1993, 115, 2507-2508.
13. (a) Kawashima, T.; Ohno, F.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2094-2095.
14. (b) Kawashima, T.; Ohno, F.; Okazaki, R. J. Am. Chem. Soc. 1993, 115, 10434-10435.
15. For the Corey-Chaykovsky reactions, see: (a) Aubé, J. In Comprehensive Organic Synthesis: Selectivity, Strategy, and Efficiency in Modern Synthetic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 822-825. For the related reactions of aminosulfoxonium ylides, see: (b) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341-347.
16. For the Corey-Chaykovsky reactions, see: (a) Aubé, J. In Comprehensive Organic Synthesis: Selectivity, Strategy, and Efficiency in Modern Synthetic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 822-825. For the related reactions of aminosulfoxonium ylides, see: (b) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341-347.
17. For previous examples of sulfurane oxides, see: (a) Martin, J. C.; Perrozi, E. F. J. Am. Chem. Soc. 1974, 96, 3155-3168. (b) Perrozi, E. F.; Martin, J. C.; Paul, I. C. Ibid. 1974, 96, 6735-6744. (c) Lau, P. H. W.; Martin, J. C. Ibid. 1977, 99, 5490-5491. (d) Rongione, J. C.; Martin, J. C. Ibid. 1990, 112, 1637-1638.
18. For previous examples of sulfurane oxides, see: (a) Martin, J. C.; Perrozi, E. F. J. Am. Chem. Soc. 1974, 96, 3155-3168. (b) Perrozi, E. F.; Martin, J. C.; Paul, I. C. Ibid. 1974, 96, 6735-6744. (c) Lau, P. H. W.; Martin, J. C. Ibid. 1977, 99, 5490-5491. (d) Rongione, J. C.; Martin, J. C. Ibid. 1990, 112, 1637-1638.
19. For previous examples of sulfurane oxides, see: (a) Martin, J. C.; Perrozi, E. F. J. Am. Chem. Soc. 1974, 96, 3155-3168. (b) Perrozi, E. F.; Martin, J. C.; Paul, I. C. Ibid. 1974, 96, 6735-6744. (c) Lau, P. H. W.; Martin, J. C. Ibid. 1977, 99, 5490-5491. (d) Rongione, J. C.; Martin, J. C. Ibid. 1990, 112, 1637-1638.
20. For previous examples of sulfurane oxides, see: (a) Martin, J. C.; Perrozi, E. F. J. Am. Chem. Soc. 1974, 96, 3155-3168. (b) Perrozi, E. F.; Martin, J. C.; Paul, I. C. Ibid. 1974, 96, 6735-6744. (c) Lau, P. H. W.; Martin, J. C. Ibid. 1977, 99, 5490-5491. (d) Rongione, J. C.; Martin, J. C. Ibid. 1990, 112, 1637-1638.
21. 4, ozone, and dimethyldioxirane was unsuccessful.
22. 3S: C. 41.77; H, 1.84; S, 5.87. Found: C, 41.70; H, 2.08; S, 6.35.
23. This bidentate ligand is very effective in stabilizing the higher coordination states of nonmetallic elements; see: 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, 1049-1053.
24. Granoth, I.; Martin, J. C. J. Am. Chem. Soc. 1981, 103, 2711-2715.
25. w = 0.049). Full details of the cristallographic structure analyses are described in the supporting information.
26. 3b
27. 2 with formaldehyde; see: Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1-14.