Formation of a pentacoordinate 1,2-oxastannetanide by novel base-induced rearrangement of a bis(β-hydroxyalkyl)stannane

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 124, Issue , 1997, Pages 513-516

  Naganuma, Kenji ^a   Kawashima, Takayuki ^a   Okazaki, Renji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Bis( hydroxyalkyl)stannane; Homo Brook type rearrangement; Oxastannetane; Pentacoordinate stannate; Tin Peterson reaction

Indexed keywords

EID: 0005780169     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509708545672     Document Type: Article

References (14)

1. T. Kawashima and R. Okazaki, Synlett, 1996, 600 and references cited therein.
2. (a) T. Kawashima, K. Kato, and R. Okazaki, J. Am. Chem. Soc., 114, 4008 (1992);
3. (b) T. Kawashima, K. Kato, R. Okazaki, Angew. Chem., Int. Ed. Engl., 32, 869 (1993).
4. T. Kawashima, N. Iwama, and R. Okazaki, J. Am. Chem. Soc., 114, 7598 (1992).
5. T. Kawashima, N. Iwama, and R. Okazaki, J. Am. Chem. Soc., 115, 2507 (1993).
6. T. Kawashima, R. Okazaki, and R. Okazaki, Angew. Chem., Int. Ed. Engl., in press.
7. T. Hiiro, Y. Atarashi, N. Kambe, S. -I. Fujiwara, A. Ogawa, I. Ryu, and N. Sonoda, Organometallics, 9, 1355 (1990).
8. Generation of the dianion by the reaction of bis(iodomethyl)dimethylstannane with n-BuLi has been reported. H. Schumann, R. Mohtachemi, and M. Schwichtenberg, Z. Naturforsh. B 43. 1510 (1988).
9. For 1,3-migration of a silyl group from carbon to oxygen, see: P. F. Hudrlik, G., A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982), K. Yamamoto, and Y. Tomo, Tetrahedron Lett., 24, 1997 (1983); F. Sato, Y. Tanaka, and M. Sato, J. Chem. Soc., Chem. Commun., 1983, 165; S. R. Wilson, and G. M. Georgiadis, J. Org. Chem., 48, 4143 (1983); K. Yamamoto, T. Kimura, and Y. Tomo, Tetrahedron Lett., 26, 4505 (1985); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993).
10. For 1,3-migration of a silyl group from carbon to oxygen, see: P. F. Hudrlik, G., A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982), K. Yamamoto, and Y. Tomo, Tetrahedron Lett., 24, 1997 (1983); F. Sato, Y. Tanaka, and M. Sato, J. Chem. Soc., Chem. Commun., 1983, 165; S. R. Wilson, and G. M. Georgiadis, J. Org. Chem., 48, 4143 (1983); K. Yamamoto, T. Kimura, and Y. Tomo, Tetrahedron Lett., 26, 4505 (1985); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993).
11. For 1,3-migration of a silyl group from carbon to oxygen, see: P. F. Hudrlik, G., A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982), K. Yamamoto, and Y. Tomo, Tetrahedron Lett., 24, 1997 (1983); F. Sato, Y. Tanaka, and M. Sato, J. Chem. Soc., Chem. Commun., 1983, 165; S. R. Wilson, and G. M. Georgiadis, J. Org. Chem., 48, 4143 (1983); K. Yamamoto, T. Kimura, and Y. Tomo, Tetrahedron Lett., 26, 4505 (1985); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993).
12. For 1,3-migration of a silyl group from carbon to oxygen, see: P. F. Hudrlik, G., A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982), K. Yamamoto, and Y. Tomo, Tetrahedron Lett., 24, 1997 (1983); F. Sato, Y. Tanaka, and M. Sato, J. Chem. Soc., Chem. Commun., 1983, 165; S. R. Wilson, and G. M. Georgiadis, J. Org. Chem., 48, 4143 (1983); K. Yamamoto, T. Kimura, and Y. Tomo, Tetrahedron Lett., 26, 4505 (1985); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993).
13. For 1,3-migration of a silyl group from carbon to oxygen, see: P. F. Hudrlik, G., A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982), K. Yamamoto, and Y. Tomo, Tetrahedron Lett., 24, 1997 (1983); F. Sato, Y. Tanaka, and M. Sato, J. Chem. Soc., Chem. Commun., 1983, 165; S. R. Wilson, and G. M. Georgiadis, J. Org. Chem., 48, 4143 (1983); K. Yamamoto, T. Kimura, and Y. Tomo, Tetrahedron Lett., 26, 4505 (1985); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993).
14. For 1,3-migration of a silyl group from carbon to oxygen, see: P. F. Hudrlik, G., A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982), K. Yamamoto, and Y. Tomo, Tetrahedron Lett., 24, 1997 (1983); F. Sato, Y. Tanaka, and M. Sato, J. Chem. Soc., Chem. Commun., 1983, 165; S. R. Wilson, and G. M. Georgiadis, J. Org. Chem., 48, 4143 (1983); K. Yamamoto, T. Kimura, and Y. Tomo, Tetrahedron Lett., 26, 4505 (1985); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993).