Small ring compounds containing highly coordinate Group 14 elements

Journal of Organometallic Chemistry

Volumn 611, Issue 1-2, 2000, Pages 256-263

  Kawashima, Takayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Homo Brook rearrangement; Olefin formation; Pentacoordinate 1,2 oxagermetanide; Pentacoordinate 1,2 oxasiletanide; Pentacoordinate 1,2 oxastannetanide; Peterson type reactions; X ray crystallographic analysis

Indexed keywords

EID: 0000403006     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00491-5     Document Type: Article

References (74)

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34. For reviews, see: (a) A. Maercker, Org. React. (N.Y.) 14 (1965) 270. (b) D.J.H. Smith, in: D.H.R. Barton, W.D. Ollis (Eds.), Comprehensive Organic Chemistry, Vol. 2, Pergamon, Oxford, 1979, pp. 1316-1329. (c) I. Gosney, A.G. Rowley, in: J.I.G. Cadogan (Ed.), Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979, pp. 17-153;. (d) B.E. Maryanoff, A.B. Reitz, Phosphorus Sulfur Silicon 27 (1986) 167. (e) B.E. Maryanoff, A.B. Reitz, Chem. Rev. 89 (1989) 863. (f) E. Vedejs, M.J. Peterson, Top. Stereochem. 21 (1994) 1.
35. For reviews, see: (a) A. Maercker, Org. React. (N.Y.) 14 (1965) 270. (b) D.J.H. Smith, in: D.H.R. Barton, W.D. Ollis (Eds.), Comprehensive Organic Chemistry, Vol. 2, Pergamon, Oxford, 1979, pp. 1316-1329. (c) I. Gosney, A.G. Rowley, in: J.I.G. Cadogan (Ed.), Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979, pp. 17-153;. (d) B.E. Maryanoff, A.B. Reitz, Phosphorus Sulfur Silicon 27 (1986) 167. (e) B.E. Maryanoff, A.B. Reitz, Chem. Rev. 89 (1989) 863. (f) E. Vedejs, M.J. Peterson, Top. Stereochem. 21 (1994) 1.
36. For reviews, see: (a) A. Maercker, Org. React. (N.Y.) 14 (1965) 270. (b) D.J.H. Smith, in: D.H.R. Barton, W.D. Ollis (Eds.), Comprehensive Organic Chemistry, Vol. 2, Pergamon, Oxford, 1979, pp. 1316-1329. (c) I. Gosney, A.G. Rowley, in: J.I.G. Cadogan (Ed.), Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979, pp. 17-153;. (d) B.E. Maryanoff, A.B. Reitz, Phosphorus Sulfur Silicon 27 (1986) 167. (e) B.E. Maryanoff, A.B. Reitz, Chem. Rev. 89 (1989) 863. (f) E. Vedejs, M.J. Peterson, Top. Stereochem. 21 (1994) 1.
37. For reviews, see: (a) A. Maercker, Org. React. (N.Y.) 14 (1965) 270. (b) D.J.H. Smith, in: D.H.R. Barton, W.D. Ollis (Eds.), Comprehensive Organic Chemistry, Vol. 2, Pergamon, Oxford, 1979, pp. 1316-1329. (c) I. Gosney, A.G. Rowley, in: J.I.G. Cadogan (Ed.), Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979, pp. 17-153;. (d) B.E. Maryanoff, A.B. Reitz, Phosphorus Sulfur Silicon 27 (1986) 167. (e) B.E. Maryanoff, A.B. Reitz, Chem. Rev. 89 (1989) 863. (f) E. Vedejs, M.J. Peterson, Top. Stereochem. 21 (1994) 1.
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43. For the bidentate ligand which is very effective in stabilizing the higher coordination states of nonmetallic elements, see: (a) E.F. Perozzi, R.S. Michalak, G.D. Figuly, W.H. Stevenson III, D.B. Dess, M.R. Ross, J.C. Martin, J. Org. Chem. 46 (1981) 1049. For sulfurane oxides, see: (b) J.C. Martin, E.F. Perozzi, Science 191 (1976) 154. For organo-nonmetallic species, see: (c) J.C. Martin, Science 221 (1983) 509. For 10-Ge-5, see: (d) S.E. Denmark, R.T. Jacobs, G. Dai-Ho, S. Wilson, Organometallics 9 (1990) 3015. For 10-Si-5, see: (e) W.H. Stevenson III, S. Wilson, J.C. Martin, W.B. Farnham, J. Am. Chem. Soc. 107 (1985) 6340.
44. For the bidentate ligand which is very effective in stabilizing the higher coordination states of nonmetallic elements, see: (a) E.F. Perozzi, R.S. Michalak, G.D. Figuly, W.H. Stevenson III, D.B. Dess, M.R. Ross, J.C. Martin, J. Org. Chem. 46 (1981) 1049. For sulfurane oxides, see: (b) J.C. Martin, E.F. Perozzi, Science 191 (1976) 154. For organo-nonmetallic species, see: (c) J.C. Martin, Science 221 (1983) 509. For 10-Ge-5, see: (d) S.E. Denmark, R.T. Jacobs, G. Dai-Ho, S. Wilson, Organometallics 9 (1990) 3015. For 10-Si-5, see: (e) W.H. Stevenson III, S. Wilson, J.C. Martin, W.B. Farnham, J. Am. Chem. Soc. 107 (1985) 6340.
45. For the bidentate ligand which is very effective in stabilizing the higher coordination states of nonmetallic elements, see: (a) E.F. Perozzi, R.S. Michalak, G.D. Figuly, W.H. Stevenson III, D.B. Dess, M.R. Ross, J.C. Martin, J. Org. Chem. 46 (1981) 1049. For sulfurane oxides, see: (b) J.C. Martin, E.F. Perozzi, Science 191 (1976) 154. For organo-nonmetallic species, see: (c) J.C. Martin, Science 221 (1983) 509. For 10-Ge-5, see: (d) S.E. Denmark, R.T. Jacobs, G. Dai-Ho, S. Wilson, Organometallics 9 (1990) 3015. For 10-Si-5, see: (e) W.H. Stevenson III, S. Wilson, J.C. Martin, W.B. Farnham, J. Am. Chem. Soc. 107 (1985) 6340.
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57. For silyl group migration from carbon to oxygen, see: (a) K. Yamamoto, Y. Tomo, Tetrahedron Lett. 24 (1983) 1997. (b) F. Sato, Y. Tanaka, M. Sato, J. Chem. Soc. Chem. Commun. (1983) 165. (c) S.R. Wilson, G.M. Georgiadis, J. Org. Chem. 48 (1983) 4143. (d) K. Yamamoto, T. Kimura, Y. Tomo, Tetrahedron Lett. 26 (1985) 4505. (e) H. Shinokubo, K. Miura, K. Oshima, K. Utimoto, Tetrahedron Lett. 34 (1993) 1951. (f) H. Shinokubo, K. Oshima, K. Utimoto, Chem. Lett. (1995) 461.
58. For silyl group migration from carbon to oxygen, see: (a) K. Yamamoto, Y. Tomo, Tetrahedron Lett. 24 (1983) 1997. (b) F. Sato, Y. Tanaka, M. Sato, J. Chem. Soc. Chem. Commun. (1983) 165. (c) S.R. Wilson, G.M. Georgiadis, J. Org. Chem. 48 (1983) 4143. (d) K. Yamamoto, T. Kimura, Y. Tomo, Tetrahedron Lett. 26 (1985) 4505. (e) H. Shinokubo, K. Miura, K. Oshima, K. Utimoto, Tetrahedron Lett. 34 (1993) 1951. (f) H. Shinokubo, K. Oshima, K. Utimoto, Chem. Lett. (1995) 461.
59. For silyl group migration from carbon to oxygen, see: (a) K. Yamamoto, Y. Tomo, Tetrahedron Lett. 24 (1983) 1997. (b) F. Sato, Y. Tanaka, M. Sato, J. Chem. Soc. Chem. Commun. (1983) 165. (c) S.R. Wilson, G.M. Georgiadis, J. Org. Chem. 48 (1983) 4143. (d) K. Yamamoto, T. Kimura, Y. Tomo, Tetrahedron Lett. 26 (1985) 4505. (e) H. Shinokubo, K. Miura, K. Oshima, K. Utimoto, Tetrahedron Lett. 34 (1993) 1951. (f) H. Shinokubo, K. Oshima, K. Utimoto, Chem. Lett. (1995) 461.
60. For silyl group migration from carbon to oxygen, see: (a) K. Yamamoto, Y. Tomo, Tetrahedron Lett. 24 (1983) 1997. (b) F. Sato, Y. Tanaka, M. Sato, J. Chem. Soc. Chem. Commun. (1983) 165. (c) S.R. Wilson, G.M. Georgiadis, J. Org. Chem. 48 (1983) 4143. (d) K. Yamamoto, T. Kimura, Y. Tomo, Tetrahedron Lett. 26 (1985) 4505. (e) H. Shinokubo, K. Miura, K. Oshima, K. Utimoto, Tetrahedron Lett. 34 (1993) 1951. (f) H. Shinokubo, K. Oshima, K. Utimoto, Chem. Lett. (1995) 461.
61. For silyl group migration from carbon to oxygen, see: (a) K. Yamamoto, Y. Tomo, Tetrahedron Lett. 24 (1983) 1997. (b) F. Sato, Y. Tanaka, M. Sato, J. Chem. Soc. Chem. Commun. (1983) 165. (c) S.R. Wilson, G.M. Georgiadis, J. Org. Chem. 48 (1983) 4143. (d) K. Yamamoto, T. Kimura, Y. Tomo, Tetrahedron Lett. 26 (1985) 4505. (e) H. Shinokubo, K. Miura, K. Oshima, K. Utimoto, Tetrahedron Lett. 34 (1993) 1951. (f) H. Shinokubo, K. Oshima, K. Utimoto, Chem. Lett. (1995) 461.
62. For silyl group migration from carbon to oxygen, see: (a) K. Yamamoto, Y. Tomo, Tetrahedron Lett. 24 (1983) 1997. (b) F. Sato, Y. Tanaka, M. Sato, J. Chem. Soc. Chem. Commun. (1983) 165. (c) S.R. Wilson, G.M. Georgiadis, J. Org. Chem. 48 (1983) 4143. (d) K. Yamamoto, T. Kimura, Y. Tomo, Tetrahedron Lett. 26 (1985) 4505. (e) H. Shinokubo, K. Miura, K. Oshima, K. Utimoto, Tetrahedron Lett. 34 (1993) 1951. (f) H. Shinokubo, K. Oshima, K. Utimoto, Chem. Lett. (1995) 461.
63. (a) P.F. Hudrlik, G.A. Nagendrappa, K. Kulkarni, A.M. Hudrlik, Tetrahedron Lett. (1979) 2237.
64. (b) P.F. Hudrlik, A.M. Hudrlik, A.K. Kulkarni, J. Am. Chem. Soc. 104 (1982) 6809.
65. (a) K. Naganuma, T. Kawashima, R. Okazaki, Chem. Lett. (1999) 1139.
66. (b) K. Naganuma, D. Sci. Thesis, the University of Tokyo, Tokyo, Japan (2000). Although the correct structure of trans-1e is an enantiomer of the structure as shown in Scheme 7, the structure was used conveniently in order to fix the configuration of the silicon center.
67. No reaction took place when 1b was treated with acetic acid at room temperature in sharp contrast to 1a (see text).
68. For Brook rearrangement, see; A.G. Brook, Ace. Chem. Res. 7 (1974) 77. For reverse Brook rearrangement, see: R. West, R. Lowe, H.F. Stewart, A. Wright, J. Am. Chem. Soc. 93 (1971) 282; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3214; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3227; R.J. Linderman, A. Ghannam, J. Org. Chem. 53 (1988) 2878; R.J. Linderman, A. Ghannam, J. Am. Chem. Soc. 112 (1990) 2392.
69. For Brook rearrangement, see; A.G. Brook, Ace. Chem. Res. 7 (1974) 77. For reverse Brook rearrangement, see: R. West, R. Lowe, H.F. Stewart, A. Wright, J. Am. Chem. Soc. 93 (1971) 282; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3214; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3227; R.J. Linderman, A. Ghannam, J. Org. Chem. 53 (1988) 2878; R.J. Linderman, A. Ghannam, J. Am. Chem. Soc. 112 (1990) 2392.
70. For Brook rearrangement, see; A.G. Brook, Ace. Chem. Res. 7 (1974) 77. For reverse Brook rearrangement, see: R. West, R. Lowe, H.F. Stewart, A. Wright, J. Am. Chem. Soc. 93 (1971) 282; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3214; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3227; R.J. Linderman, A. Ghannam, J. Org. Chem. 53 (1988) 2878; R.J. Linderman, A. Ghannam, J. Am. Chem. Soc. 112 (1990) 2392.
71. For Brook rearrangement, see; A.G. Brook, Ace. Chem. Res. 7 (1974) 77. For reverse Brook rearrangement, see: R. West, R. Lowe, H.F. Stewart, A. Wright, J. Am. Chem. Soc. 93 (1971) 282; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3214; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3227; R.J. Linderman, A. Ghannam, J. Org. Chem. 53 (1988) 2878; R.J. Linderman, A. Ghannam, J. Am. Chem. Soc. 112 (1990) 2392.
72. For Brook rearrangement, see; A.G. Brook, Ace. Chem. Res. 7 (1974) 77. For reverse Brook rearrangement, see: R. West, R. Lowe, H.F. Stewart, A. Wright, J. Am. Chem. Soc. 93 (1971) 282; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3214; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3227; R.J. Linderman, A. Ghannam, J. Org. Chem. 53 (1988) 2878; R.J. Linderman, A. Ghannam, J. Am. Chem. Soc. 112 (1990) 2392.
73. For Brook rearrangement, see; A.G. Brook, Ace. Chem. Res. 7 (1974) 77. For reverse Brook rearrangement, see: R. West, R. Lowe, H.F. Stewart, A. Wright, J. Am. Chem. Soc. 93 (1971) 282; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3214; A. Wright, R. West, J. Am. Chem. Soc. 96 (1974) 3227; R.J. Linderman, A. Ghannam, J. Org. Chem. 53 (1988) 2878; R.J. Linderman, A. Ghannam, J. Am. Chem. Soc. 112 (1990) 2392.
74. K. Naganuma, T. Kawashima, The 12th International Symposium on Organosilicon Chemistry, Sendai, May, 1999, Abstracts, p. 173.