Experimental and theoretical evidence for oxirane formation reaction of pentacoordinate 1, 2γ6-oxathietanes with retention of configuration

Journal of the American Chemical Society

Volumn 118, Issue 49, 1996, Pages 12455-12456

  Kawashima, Takayuki ^a   Ohno, Fumihiko ^a   Okazaki, Renji ^a   Ikeda, Hirotaka ^b   Inagaki, Satoshi ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 OXATHIETANE DERIVATIVE; CYCLOBUTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030457354     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9629975     Document Type: Article

References (43)

1. Kawashima, T.; Okazaki, R. Synlett 1996, 600-608.
2. For pentacoordinate 1,2-oxaphosphetanes, see: Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869-870.
3. Kawashima, T.; Takami, H.; Okazaki, R. J. Am. Chem. Soc. 1994, 116, 4509-4510.
4. For oxetanes having pentacoordinate group 14 elements, see: Kawashima, T.; Iwama, N.;
5. Okazaki, R. Ibid. 1992, 114, 7598-7599.
6. Kawashima, T.; Nishiwaki, Y.; Okazaki, R. J. Organomet. Chem. 1995, 499, 143-146.
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9. For tetracoordinate 1,2-oxachalcogenetanes, see: (a) Kawashima, T.; Ohno, F.; Okazaki, R. J. Am. Chem. Soc. 1993, 115, 10434-10435.
10. (b) Kawashima, T.; Ohno, F.; Okazaki, R. Angew. Chem, Int. Ed. Engl. 1994, 33, 2094-2095.
11. Ohno, F.; Kawashima, T.; Okazaki, R. J. Am. Chem. Soc. 1996, 118, 697-698.
12. This compound can be classified to sulfurane oxides. For previous examples, see: Martin, J. C.; Perozzi, E. F. J. Am. Chem. Soc. 1974, 96, 3155-3168.
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33. In the formation reaction of spiropentanes by the reaction of sulfonium cyclopropylides with carbonyl compounds, a mechanism involving an oxathietane was proposed as an alternative one involving a ring expansion to a σ-sulfurane having an oxirane ring followed by reductive elimination of the sulfide, see: Bogdanowicz, M. J.; Trost, B. M. Tetrahedron Lett. 1970, 887-890.
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35. For the bidentate ligand which 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., Ill; Dess, D. B.; Ross, M. R.; Martin, J. C. J. Org. Chem. 1981, 46, 1049-1053.
36. Products 5, 10, 12, and 13 are thought to be formed via a mechanism similar to that reported in ref 2b. Benzaldehyde (11) and 14 seem to be formed as follows: the oxosulfonium ylide, which is formed by retroaddition of 3 together with 5, reacts with 13 to give 14 and the corresponding inner oxosulfonium oxide, which undergoes C-S bond cleavage to afford 11 and 12.
37. Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 709, 1-14.
38. The first example was reported in ref 5a, but the reaction was considered to proceed via a betaine.
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40. -1).
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42. The ligand-coupling reactions involving a sulfurane intermediate have been reported. For a recent review, see: Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202-208.
43. For a recent example of the ligand coupling reaction from sulfuranes which was spectroscopically identified, see: Ogawa, S.; Sato, S.; Furukawa, N. Tetrahedron Lett. 1992, 33, 7925-7928.