Highly stereoselective synthesis of bicyclo[n.3.0]alkanes by titanium tetrachloride promoted [3 + 2] cycloaddition of allylsilanes and 1-acetylcycloalkenes

Chemistry - A European Journal

Volumn 3, Issue 4, 1997, Pages 538-551

  Knölker, Hans Joachim ^a   Foitzik, Norbert ^a   Goesmann, Helmut ^a   Graf, Regina ^a   Jones, Peter G ^b   Wanzl, Günter ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

allylsilanes; bicycloalkanes; cycloaddition; diastereoselective synthesis; enones

Indexed keywords

EID: 0041102806     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030409     Document Type: Article

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29. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
30. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
31. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
32. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
33. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
34. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
35. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
36. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
37. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
38. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852; M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301; D. Seyferth, D. L. White, J. Am. Chem. Soc. 1972, 94, 3132; E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, p. 19, 32; for more recent reports of cationic 1,2 silyl shifts, see: J. K. Whitesell, K. Nabona, D. Deyo, J. Org. Chem. 1989, 54, 2258; R. F. Cunico, ibid. 1990, 55, 4474; J. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868; S. Yamazaki, S. Katoh, S. Yamabe, J. Org. Chem. 1992, 57, 4; J. S. Panek, R. Beresis, ibid. 1993, 58, 809; J. S. Panek, R. T. Beresis, J. Am. Chem. Soc. 1993, 115, 7898; T. Akiyama; K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627; S. Yamazaki, M. Tanaka, A. Yamaguchi, S. Yamabe, J. Am. Chem. Soc. 1994, 116, 2356; J. S. Panek, N. F. Jain, J. Org. Chem. 1994, 59, 2674; S. R. Angle, J. P. Boyce, Tetrahedron Lett. 1994, 35, 6461; A. Stahl, E. Steckhan, M. Nieger, ibid. 1994, 35, 7371; T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, ibid. 1994, 35, 8401.
39. a) R. L. Danheiser, B. R. Dixon, R. W. Gleason, J. Org. Chem. 1992, 57, 6094;
40. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
41. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
42. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
43. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
44. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
45. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
46. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
47. b) K. Ohkata, K. Ishimaru, Y.-G. Lee, K.-y. Akiba, Chem. Lett. 1990, 1725; Y-G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K.-y. Akiba, J. Org. Chem. 1991, 56, 2058; B. B. Snider, Q. Zhang, ibid. 1991, 56, 4908; J. Ipaktschi, A. Heydari, Angew. Chem. 1992, 104, 335; Angew. Chem. Int. Ed. 1992, 31, 313; J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; M.-J. Wu, J.-Y. Yeh. Tetrahedron 1994, 50, 1073.
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57. a) W. Hanstein, H. J. Berwin, T. G. Traylor, J. Am. Chem. Soc. 1970, 92, 829; T. G. Traylor, W. Hanstein, H. J. Berwin, N. A. Clinton, R. S. Brown, ibid. 1971, 93, 5715;
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59. b) S. G. Wierschke, J. Chandrasekhar, W. L. Jorgensen, ibid. 1985, 107, 1496; M. R. Ibrahim, W. L. Jorgensen, ibid. 1989, 111, 819; T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161; J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120: J. M. White, G. B. Robertson, J. Org. Chem. 1992, 57, 4638; J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317. For an excellent review on this topic, see: J. B. Lambert, Tetrahedron 1990, 46, 2677.
60. b) S. G. Wierschke, J. Chandrasekhar, W. L. Jorgensen, ibid. 1985, 107, 1496; M. R. Ibrahim, W. L. Jorgensen, ibid. 1989, 111, 819; T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161; J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120: J. M. White, G. B. Robertson, J. Org. Chem. 1992, 57, 4638; J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317. For an excellent review on this topic, see: J. B. Lambert, Tetrahedron 1990, 46, 2677.
61. b) S. G. Wierschke, J. Chandrasekhar, W. L. Jorgensen, ibid. 1985, 107, 1496; M. R. Ibrahim, W. L. Jorgensen, ibid. 1989, 111, 819; T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161; J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120: J. M. White, G. B. Robertson, J. Org. Chem. 1992, 57, 4638; J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317. For an excellent review on this topic, see: J. B. Lambert, Tetrahedron 1990, 46, 2677.
62. b) S. G. Wierschke, J. Chandrasekhar, W. L. Jorgensen, ibid. 1985, 107, 1496; M. R. Ibrahim, W. L. Jorgensen, ibid. 1989, 111, 819; T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161; J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120: J. M. White, G. B. Robertson, J. Org. Chem. 1992, 57, 4638; J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317. For an excellent review on this topic, see: J. B. Lambert, Tetrahedron 1990, 46, 2677.
63. b) S. G. Wierschke, J. Chandrasekhar, W. L. Jorgensen, ibid. 1985, 107, 1496; M. R. Ibrahim, W. L. Jorgensen, ibid. 1989, 111, 819; T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161; J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120: J. M. White, G. B. Robertson, J. Org. Chem. 1992, 57, 4638; J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317. For an excellent review on this topic, see: J. B. Lambert, Tetrahedron 1990, 46, 2677.
64. b) S. G. Wierschke, J. Chandrasekhar, W. L. Jorgensen, ibid. 1985, 107, 1496; M. R. Ibrahim, W. L. Jorgensen, ibid. 1989, 111, 819; T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161; J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120: J. M. White, G. B. Robertson, J. Org. Chem. 1992, 57, 4638; J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317. For an excellent review on this topic, see: J. B. Lambert, Tetrahedron 1990, 46, 2677.
65. b) S. G. Wierschke, J. Chandrasekhar, W. L. Jorgensen, ibid. 1985, 107, 1496; M. R. Ibrahim, W. L. Jorgensen, ibid. 1989, 111, 819; T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161; J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120: J. M. White, G. B. Robertson, J. Org. Chem. 1992, 57, 4638; J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317. For an excellent review on this topic, see: J. B. Lambert, Tetrahedron 1990, 46, 2677.
66. The bridged pentavalent silicon cation should be referred to as a "siliranium ion" (or "siloniacyclopropane"), but not "siliconium ion" or "silacyclopropylium cation".
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69. Review: T. K. Sarkar, Synthesis 1990, 969, 1101. Method A: J. P. Pillot, J. Dunoguès, R. Calas, Tetrahedron Lett. 1976, 1871. Method B: T. Hayashi, K. Kabeta, M. Kumada, Tetrahedron Lett. 1984, 25, 1499; T. Hayashi, M. Konishi, K.-i. Yokota, M. Kumada, Chem. Lett. 1980, 767; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1970, 213; L. M. Venanzi, J. Chem. Soc. 1958, 719.
70. Review: T. K. Sarkar, Synthesis 1990, 969, 1101. Method A: J. P. Pillot, J. Dunoguès, R. Calas, Tetrahedron Lett. 1976, 1871. Method B: T. Hayashi, K. Kabeta, M. Kumada, Tetrahedron Lett. 1984, 25, 1499; T. Hayashi, M. Konishi, K.-i. Yokota, M. Kumada, Chem. Lett. 1980, 767; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1970, 213; L. M. Venanzi, J. Chem. Soc. 1958, 719.
71. Review: T. K. Sarkar, Synthesis 1990, 969, 1101. Method A: J. P. Pillot, J. Dunoguès, R. Calas, Tetrahedron Lett. 1976, 1871. Method B: T. Hayashi, K. Kabeta, M. Kumada, Tetrahedron Lett. 1984, 25, 1499; T. Hayashi, M. Konishi, K.-i. Yokota, M. Kumada, Chem. Lett. 1980, 767; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1970, 213; L. M. Venanzi, J. Chem. Soc. 1958, 719.
72. Review: T. K. Sarkar, Synthesis 1990, 969, 1101. Method A: J. P. Pillot, J. Dunoguès, R. Calas, Tetrahedron Lett. 1976, 1871. Method B: T. Hayashi, K. Kabeta, M. Kumada, Tetrahedron Lett. 1984, 25, 1499; T. Hayashi, M. Konishi, K.-i. Yokota, M. Kumada, Chem. Lett. 1980, 767; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1970, 213; L. M. Venanzi, J. Chem. Soc. 1958, 719.
73. Review: T. K. Sarkar, Synthesis 1990, 969, 1101. Method A: J. P. Pillot, J. Dunoguès, R. Calas, Tetrahedron Lett. 1976, 1871. Method B: T. Hayashi, K. Kabeta, M. Kumada, Tetrahedron Lett. 1984, 25, 1499; T. Hayashi, M. Konishi, K.-i. Yokota, M. Kumada, Chem. Lett. 1980, 767; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1970, 213; L. M. Venanzi, J. Chem. Soc. 1958, 719.
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75. For reviews on the oxidative cleavage of carbon - silicon bonds, see: D. Schinzer, Nachr. Chem. Tech. Lab. 1989, 37, 263; I. Fleming, Pure Appl. Chem. 1990, 62, 1879; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599.
76. For reviews on the oxidative cleavage of carbon - silicon bonds, see: D. Schinzer, Nachr. Chem. Tech. Lab. 1989, 37, 263; I. Fleming, Pure Appl. Chem. 1990, 62, 1879; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599.
77. Further details of the crystal structure investigations may be obtained from the Fachinformationszentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen (Germany) on quoting the CSD numbers given.
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