Reactive Intermediate Chemistry

REFERENCES 707

Soc., Dalton Trans. 1998, 2939. (q) M. Weidenbruch, Eur. J. Inorg. Chem. 1999, 373.

(r)N. Tokitoh and R. Okazaki, Coord. Chem. Rev. 2000, 210, 251. (s) M. Haaf, T. A. Schmedake, and R. West, Acc. Chem. Res. 2000, 33, 704. (t) P. P. Gaspar, in Science of Synthesis, Vol. 4.4.3, Thieme, Stuttgart, 2002, p. 135.

6.(a) W. H. Atwell and D. R. Weynberg, J. Organometal. Chem. 1966, 5, 594. (b) W. H. Atwell and D. R. Weynberg, Angew. Chem., Int. Ed. Engl. 1969, 8, 469.

7.I. M. T. Davidson, K. J. Huges, and S. Ijadi-Maghsoodi, Organometallics 1986, 6, 639.

8.J. H. Gilman, S. G. Cottis, and W. H. Atwell, J. Am. Chem. Soc. 1964, 86, 1596.

9.(a) W. P. Neumann and M. Schriewer, Tetrahedron Lett. 1980, 21, 3273. (b) M. Schriewer and W. P. Neumann, Angew. Chem., Int. Ed. Engl. 1981, 20, 1019. (c) M. Schriewer and W. P. Neumann, J. Am. Chem. Soc. 1983, 105, 897.

10.(a) W. Ando, T. Tsumuraya, and A. Sekiguchi, Chem. Lett. 1987, 317. (b) Y. Kabe and W. Ando, Adv. Strain Org. Chem. 1993, 3, 59.

11.D. Seyferth, D. C. Annarelli, and S. C. Vick, J. Am. Chem. Soc. 1976, 98, 6382.

12.D. Seyferth and S. C. Vick, J. Organometal. Chem. 1977, 125, C11.

13.P. Boudjouk, R. Samaraweera, R. Sooriyakumaran, J. Chrusciel, and K. R. Anderson,

Angew. Chem., Int. Ed. Engl. 1988, 27, 1355.

14.R. L. Lambert and D. Seyferth, J. Am. Chem. Soc. 1972, 94, 9246.

15.D. Seyferth and D. C. Annarelli, J. Am. Chem. Soc. 1975, 97, 325.

16.(a) E. A. Chernyshev, N. G. Komalenkova, and S. A. Bashikirova, J. Organometal. Chem. 1984, 271, 129. (b) D. Lei and P. P. Gaspar, Organometallics 1985, 4, 1471.

(c)M. G. Steinmetz and C. Yu, Organometallics 1992, 11, 2686.

17.M. Ishikawa, T. Fuchigami, and M. Kumada, J. Am. Chem. Soc. 1977, 99, 245.

18.H. Sakurai, Y. Kamiyama, and Y. Nakadaira, J. Am. Chem. Soc. 1977, 99, 3879.

19.T. J. Drahnak, J. Michl, and R. West, J. Am. Chem. Soc. 1979, 101, 5427.

20.(a) C. W. Carlson and R. West, Organometallics 1983, 2, 1792. (b) H. Vancik, G. Raabe, M. J. Michalczyk, R. West, and J. Michl, J. Am. Chem. Soc. 1985, 107, 4097.

21.(a) M. Ishikawa and M. Kumada, J. Chem. Soc., Chem. Commun. 1970, 612. (b) M. Ishikawa and M. Kumada, J. Chem. Soc., Chem. Commun. 1971, 489.

22.(a) P. Trefonas, R. West, and R. D. Miller, J. Am. Chem. Soc. 1985, 107, 2737. (b) G. Raabe and J. Michl, Chem. Rev. 1985, 85, 419. (c) A. G. Brook and K. M. Baines,

Adv. Organometal. Chem. 1986, 25, 1.

23.(a) M. Wakasa, I. Yoneda, and K. Mochida, J. Organometal. Chem. 1989, 366, C1. (b) K. Mochida, I. Yoneda, and M. Wakasa, J. Organometal. Chem. 1990, 399, 53.

24.S. Konieczny, S. J. Jacobs, J. K. Braddock-Wilking, and P. P. Gaspar, J. Organometal. Chem. 1988, 341, C17.

25.(a) M. Ishikawa, T. Takaoka, and M. Kumada, J. Organometal. Chem. 1972, 42, 333.

(b)M. Ishikawa and M. Kumada, Adv. Organometal. Chem. 1981, 19, 51. (c) A. G. Brook, in The Chemistry of Organosilicon Compounds, S. Patai and Z. Rappoport, Eds., John Wiley & Sons, Inc., Chichester, UK, 1989, Part 2, Chapter 15.

26.S. Masamune, Y. Hanzawa, S. Murakami, T. Bally, and F. J. Blount, J. Am. Chem. Soc. 1982, 104, 1150.

27.(a) S. Masamune, Y. Hanzawa, and D. J. Williams, J. Am. Chem. Soc., 1982, 104, 6136.

(b)J. T. Snow, S. Murakami, S. Masamune, and D. J. Williams, Tetrahedron Lett. 1984, 25, 4191. (c) S. Collins, S. Murakami, J. T. Snow, and S. Masamune, Tetrahedron Lett.

708 SILYLENES (AND GERMYLENES, STANNYLENES, PLUMBYLENES)

1985, 26, 1281. (d) M. Weidenbruch, F. T. Grim, M. Herrndorf, A. Scha¨fer, K. Peters, and S. H. Geroge, J. Organometal. Chem. 1988, 341, 335.

28.(a) W. Ando and T. Tsumuraya, Tetrahedron Lett. 1986, 27, 3251. (b) W. Ando and T. Tsumuraya, J. Chem. Soc., Chem. Commun. 1987, 1514. (c) T. Tsumuraya, S. Sato, and W. Ando, Organometallics 1988, 7, 2015. (d) T. Tsumuraya, S. Sato, and W. Ando, Organometallics 1989, 8, 161. (e) T. Tsumuraya, S. Sato, and W. Ando, Organometallics 1990, 9, 2061. (f) Y. Kabe and W. Ando, J. Organometal. Chem. 1994, 482, 131.

29.M. Ishikawa, T. Yamanaka, and M. Kumada, J. Organometal. Chem. 1985, 292, 167.

30.H. Sakurai, Y. Nakadaira, and H. Sakabe, Orgnometallics 1983, 2, 1484.

31.(a) J. A. Hawari and D. Griller, Orgnometallics 1984, 3, 1123. (b) J. A. Hawari, M. Lesage, D. Griller, and W. P. Weber, Orgnometallics 1987, 6, 880.

32.(a) P. P. Gaspar, A. M. Beatty, T. Chen, T. Haile, D. Lei, W. R. Winchester, J. BraddockWilking, N. P. Rath, W. T. Klooster, T. F. Koetzle, S. A. Mason, and A. Albinati, Organometallics 1999, 18, 3921. (b) J. A. Hawari, D. Griller, W. P. Weber, and P. P. Gaspar, J. Orgnometal. Chem. 1987, 326, 335.

33.(a) R. West, J. Organometal. Chem. 1986, 300, 327. (b) R. J. P. Corriu, G. Lanneau, C. Priou, F. Soulairol, N. Auner, R. Probst, R. Conlin, and C. J. Tan, J. Organometal. Chem. 1994, 466, 55. (c) A. Kawachi and K. Tamao, Bull. Chem. Soc. Jpn. 1997, 70, 945.

34.J. Grobe and J. Scherholt, Organosilicon Chemistry II, N. Auner and J. Weis, Eds., VCH, Weinheim, 1996, 317.

35.D. H. Pae, M. Xiao, M. Y. Chiang, and P. P. Gaspar, J. Am. Chem. Soc., 1991, 113, 1281.

36.(a) P. Jutzi, D. Kanne, and C. Kru¨ger, Angew. Chem., Int. Ed. Engl. 1986, 25, 164. (b) P. Jutzi, U. Holtmann, D. Kanne, C. Kru¨ger, Gleiter, Blom. Hyla-Krispin, R. I, Chem. Ber. 1989, 122, 1629.

37.P. Jiang and P. P. Gaspar, J. Am. Chem. Soc. 2001, 123, 8622.

38.P. P. Gaspar, M. Xiao, D. H. Pae, D. H. Berger, T. Haile, T. Chen, D. Lei, W. R. Winchester, and P. Jiang, J. Organometal. Chem. 2002, 646, 68.

39.(a) H. Ohgaki, N. Fukaya, and W. Ando, Organometallics 1997, 16, 4956. (b) M. P. Egorov, O. M. Nefedov, T.-S. Lin, and P. P. Gaspar, Organometallics 1995, 14, 1539.

40.(a) S. Patai and Z. Rappoport, Eds., The Chemistry of Organic Silicon Compounds, Part 1 and 2, John Wiley & Sons, Inc., 1989. (b) Y. Apeloig and M. Karni, in The Chemistry of Organosilicon Compounds, Vol. 2, Z. Rappoport and Y. Apeloig, Eds., John Wiley & Sons, Inc., Chichester, UK, 1998, p. 1.

41.B. T. Luke, J. A. Pole, M. B. Krogh-Jespersen, Y. Apeloig, J. Chandrasekhar, and P. v. R. Schleyer, J. Am. Chem. Soc. 1986, 108, 260.

42.B. T. Luke, J. A. Pole, M. B. Krogh-Jespersen, Y. Apeloig, M. Karni, J. Chandrasekhar, and P. v. R. Schleyer, J. Am. Chem. Soc. 1986, 108, 270.

43.J. Berkowitz, J. P. Greene, H. Cho, and R. Ruscic, J. Chem. Phys. 1987, 86, 1235.

44.M. S. Gordon, Chem. Phys. Lett. 1985, 114, 348.

45.H. J. Werner and E. A. Reinsch, J. Chem. Phys. 1982, 76, 3144.

46.T. J. Sears and P. R. Bunker, J. Chem. Phys. 1983, 79, 5265.

47.R. Janoschek, Chem. Unserer Z. 1988, 21, 128.

48.N. Wiberg, Coord. Chem. Rev. 1997, 163, 217.

49.(a) M. S. Gordon and D. R. Gano, J. Am. Chem. Soc. 1985, 106, 5421. (b) I. M. T. Davidson and R. J. Scampton, J. Organometal. Chem. 1984, 271, 249.

REFERENCES 709

50.I. Dubois, Can. J. Phys. 1968, 46, 2485.

51.H. P. Reisenauer, G. Mihm, and G. Maier, Angew. Chem., Int. Ed. Engl. 1982, 21, 854.

52.G. Maier, G. Mihm, H. P. Reisenauer, and D. L. Littman, Chem. Ber. 1984, 117, 2369.

53.G. Maier, S. Glatthaar, and H. P. Reisenauer, Chem. Ber. 1989, 122, 2403.

54.G. Maier, H. P. Reisenauer, K. Schttler, and U. Wessolek-Kraus, J. Organometal. Chem. 1989, 366, 25.

55.M. Kira, T. Maruyama, and H. Sakurai, Chem. Lett. 1993, 1345.

56.S. G. Bott, P. Marshall, P. E. Wagenseller, Y. Wang, and R. T. Conlin, J. Organometal. Chem. 1995, 499, 11.

57.M. Weidenburch, P. A. Will, K. Peters, H. G. Schnering, and H. Marsmann, J. Organometal. Chem. 1996, 521, 355.

58.M. J. Michalczyk, M. J. Fink, D. J. D. Young, C. W. Carlson, K. M. Welsh, R. West, and

J.Michl, Silicon, Germanium Tin and Lead Compd. 1986, 9, 75.

59.G. R. Gillette, G. H. Noren, and R. West, Organometallics 1987, 6, 2617.

60.K. M. Welsh, J. Michl, and R. West, J. Am. Chem. Soc. 1988, 110, 6689.

61.G. R. Gillette, G. H. Noren, and R. West, Organometallics 1990, 9, 2925.

62.G. Trinquier, J. Chem. Soc., Faraday Trans. 1993, 89, 775.

63.W. Ando, A. Sekiguchi, K. Hagiwara, A. Sakakibara, and H. Yoshida, Organometallics 1988, 8, 558.

64.T. Akasaka, W. Ando, S. Nagase, and A. Yabe, Nippon Kagaku Kaishi 1989, 1440.

65.M. A. Pearsall and R. West, J. Am. Chem. Soc. 1988, 110, 6689.

66.C. A. Arrington, J. A. Petty, S. E. Payne, and W. C. K. Haskins, J. Am. Chem. Soc. 1988, 110, 6240.

67.H. Bornemann and W. Sander, J. Organometal. Chem. 2002, 641, 156.

68.T. F. Hamilton and H. F. Schaefer, J. Chem. Phys. 1989, 90, 1031.

69.T. Akasaka, S. Nagase, A. Yabe, and W. Ando, J. Am. Chem. Soc. 1988, 110, 6270.

70.J. C. Barthelat, B. S. Roch, G. Trinquier, and J. Satge´, J. Am. Chem. Soc. 1980, 102, 4080.

71.(a) S. Tomoda, M. Shimoda, Y. Takeuchi, Y. Kaji, K. Obi, I. Tanaka, and K. Honda,

J.Chem. Soc., Chem. Commun. 1988, 910. (b) K. Mochida, N. Kanno, R. Kato,

M.Kotani, S. Yamauchi, M. Wakasa, and H. Hayashi, J. Organometal. Chem. 1991, 415, 191.

72.W. Ando, H. Itoh, T. Tsumurya, and H. Yoshida, Organometallics 1988, 7, 1880.

73.(a) W. Ando, T. Tsumuraya, and A. Sekiguchi, Chem. Lett. 1987, 317. (b) W. Ando,

H.Ito, T. Tsumuraya, and H. Yoshida, Organometallics 1988, 7, 1880.

74.W. Ando, H. Itoh, and T. Tsumurya, Organometallics 1989, 8, 2759.

75.Y. Apeloig, in The Chemistry of Organic Silicon Compounds, S. Patai and Z. Rappoport, Eds., John Wiley & Sons, Inc., Chichester, 1989.

76.H. F. Schaefer, Acc. Chem. Res. 1982, 15, 283.

77.A. Sekiguchi and W. Ando, Organometallics 1987, 6, 1857.

78.(a) A. G. Brook, in The Chemistry of Organic Silicon Compounds, S. Patai and Z. Rappoport, Eds., John Wiley & Sons, Inc., Chichester, 1989, p. 965. (b) M. G. Steinmetz,

Chem. Rev. 1995, 95, 1527.

710SILYLENES (AND GERMYLENES, STANNYLENES, PLUMBYLENES)

79.(a) M. J. Fink, D. B. Puranik, and M. P. Johnson, J. Am. Chem. Soc. 1988, 110, 1315.

(b)D. B. Puranik and M. J. Fink, J. Am. Chem. Soc. 1989, 111, 5951.

80.(a) V. N. Khabashesku, B. Balaji, S. A. Boganov, P. M. Matveichev, E. A. Chernyshev,

O.M. Nefedov, and J. Michl, Mendeleev Commun. 1992, 38. (b) V. N. Khabashesku,

B.Balaji, S. A. Boganov, O. M. Nefedov, and J. Michl, J. Am. Chem. Soc. 1994, 116, 320.

81.(a) M. E. Lee, M. A. North, and P. P. Gaspar, Phosphorus, Sulfur, and Silicon 1991, 56, 203. (b) P. P. Gaspar, in Reactive Intermediates, Vol. 3, M. Jones, Jr., and R. A. Moss, John Wiley & Sons, Inc., New York, 1985, p. 297.

82.G. Maier and J. Glathaar, in Organosilicon Chemistry-From Molecules to Materials,

N.Auner and J. Weiss, Eds., VCH, Weinhim, 1994, 131.

83.(a) A. P. Dickenson, K. E. Nares, M. A. Ring, and H. E. O’Neal, Organometallics 1987, 6, 2596. (b) G. Maier and J. Glatthaar, Angew. Chem., Int. Ed. Engl. 1994, 33, 473.

(c)G. Maier, H. Pacl, H. P. Reisenauer, A. Meudt, and R. Janoschek, J. Am. Chem. Soc. 1995, 117, 12712.

84.(a) D. Seyferth and T. F. O. Lim, J. Am. Chem. Soc. 1978, 100, 7074. (b) M.-D. Su and S.-Y. Chu, J. Phys. Chem. A. 1999, 103, 11011.

85.J. M. Jasinski, J. Chem. Phys. 1986, 5, 3057.

86.(a) K. Oka and R. Nakao, Res. Chem. Intermed. 1990, 13, 143. (b) K. Oka and R. Nakao,

J.Organometal. Chem. 1990, 390, 7.

87.Y. T. Gu and W. P. Weber, J. Organometal. Chem. 1980, 184, 7.

88.(a) M. Ishikawa, K. Nakagawa, and M. Kumada, J. Organometal. Chem. 1981, 214, 277.

(b)M. Ishikawa, M. Nakagawa, S. Katayama, and M. Kumada, J. Organometal. Chem. 1981, 216, C48.

89.(a) J. Koecher and M. Lehnig, Organometallics 1984, 3, 937. (b) J. Koecher, M. Lehnig, and W. P. Neumann, Organometallics 1988, 7, 1201.

90.W. Ando, Acc. Chem. Res. 1977, 10, 179.

91.H. Ohgaki and W. Ando, J. Orgamomet. Chem. 1996, 521, 387.

92.T. Y. Gu and W. P. Weber, J. Am. Chem. Soc., 1980, 102, 1641.

93.W. F. Goure and T. J. Barton, J. Organometal. Chem. 1980, 199, 33.

94.W. Ando, M. Ikeno, and Y. Hamada, J. Chem. Soc., Chem. Commun. 1981, 621.

95.Y. Apeloig and S. Sklenak, Can. J. Chem. 2000, 78, 1496.

96.W. H. Atwell, L. G. Mahone, S. F. Hayes, and J. G. Uhlmann, J. Organometal. Chem. 1969, 18, 69.

97.H. S. D. Soya, H. Okinoshima, and W. P. Weber, J. Organometal. Chem. 1977, 133, C-17.

98.(a) P. S. Skell and E. J. Goldstein, J. Am. Chem. Soc. 1964, 86, 1442. (b) B. Cox and

H.Purnell, J. Chem. Soc., Faraday Trans. I 1975, 71, 859.

99.D. P. Paquin and M. A. Ring, J. Am. Chem. Soc. 1977, 99, 1793.

100.S. Sakai and M. Nakamura, J. Phys. Chem. 1993, 97, 4960.

101.H. Sakurai, T. Kobayashi, and Y. Nakadira, J. Organometal. Chem. 1978, 162, C-43.

102.R. T. Conlin and P. P. Gaspar, J. Am. Chem. Soc., 1976, 98, 3715.

103.M. Ishikawa, T. Fuchikami, and M. Kumada, J. Organometal. Chem. 1977, 142, C-45.

104.A. Krebs and J. Berndt, Tetrahedron Lett. 1983, 24, 4083.

105.M. P. Egorov, M. B. Ezova, M. S. P. Kolesnikov, O. M. Nefedov, M. B. Taraban, A. I. Kruppa, and T. V. Leshina, Mendeleev Commun. 1991, 4, 143.

REFERENCES 711

106.F. Hojo, S. Sekigawa, N. Nakayama, T. Shimizu, and W. Ando, Organometallics 1993, 12, 803.

107.W. Ando, T. Shiba, T. Hidaka, K. Morihashi, and O. Kikuchi, J. Am. Chem. Soc. 1997, 119, 3629.

108.F. Meiners, W. Saak, and M. Weidenbruch, Organometallics 2000, 19, 2835

109.T. Tsumuraya and W. Ando, Organometallics 1990, 9, 869.

110.M. Ishikawa and M. Kumada, J. Organometal. Chem. 1974, 81, C-3.

111.S. Annemarie, M. Weidenbruch, and S. Pohl, J. Organometal. Chem. 1985, 282, 305.

112.W. R. Winchester and P. P. Gaspar, presented at 30th Symposium Organosilicon Chemistry, London, Ontario, Canada, 1997, p. A-16.

113.(a) W. H. Atwell and D. R. Weyenberg, J. Am. Chem. Soc. 1968, 90, 3438. (b) P. P. Gaspar, in Reactive Intermediates, Vol. 1, M. Jones, Jr. and R. A. Moss, Eds., John Wiley & Sons, New York, 1978, 229.

114.R. J. Hwang, R. T. Conlin, and P. P. Gaspar, J. Organometal. Chem. 1975, 94, C-38.

115.(a) W. Ando and H. Saso, Tetrahedron Lett. 1986, 27, 5625. (b) H. Saso and W. Ando, Chem. Lett. 1988, 1567. (c) T. Yamamoto, Y. Kabe, and W. Ando, Organometallics 1993, 12, 1996. (e) W. Ando, T. Yamamoto, H. Saso, and Y. Kabe, J. Am. Chem. Soc. 1991, 113, 2791.

116.(a) T. Akasaka, W. Ando, K. Kobayashi, and S. Nagase, J. Am. Chem. Soc. 1993, 113, 1605. (b) T. Akasaka, E. Mitsuhida, W. Ando, K. Kobayashi, and S. Nagase, J. Chem. Soc., Chem. Commun. 1995, 1529.

117.(a) W. P. Neumann, Chem. Rev. 1991, 91, 311; (b) J. Barrau, J. Excudie´, and J. Satge´, Chem. Rev. 1990, 90, 283. (c) M.-D. Su and S.-Y. Chu, J. Am. Chem. Soc. 1999, 121, 11478.

118.W. Ando, H. Ohgaki, and Y. Kabe, Angew. Chem., Int. Ed. Engl. 1994, 33, 659.

119.H. Ohgaki, Y. Kabe, and W. Ando, Organometallics 1995, 14, 2139.

120.Y. Kabe, H. Ohgaki, Y. Yamagaki, H. Nakanishi, and W. Ando, J. Organometal. Chem. 2001, 636, 82.

121.(a) W. Ando, M. Ikeno, and A. Sekiguchi, J. Am. Chem. Soc. 1977, 99, 6447. (b) W. Ando and M. Ikeno, Chem. Lett. 1978, 609.

122.W. Ando, M. Ikeno, and A. Sekiguchi, J. Am. Chem. Soc. 1978, 100, 3613.

123.(a) W. Ando, Y. Hamada, A. Sekiguchi, and K. Ueno, Tetrahedron Lett. 1982, 23, 5323.

(b)W. Ando, Y. Hamada, A. Sekiguchi, and K. Ueno, Tetrahedron Lett. 1983, 24, 4033.

124.(a) W. Ando, Y. Hamada, and A. Sekiguchi, J. Chem. Soc., Chem. Commun. 1983, 952.

(b)W. Ando, Y. Hamada, and A. Sekiguchi, Tetrahedron Lett. 1984, 25, 5057. (c) W. Ando, K. Hagiwara, and A. Sekiguchi, Organometallics 1987, 6, 2270.

125.W. Ando and M. Ikeno, J. Chem. Soc., Chem. Commun. 1979, 655.

126.(a) W. Ando, T. Tsumuraya, and A. Sekiguchi, Tetrahedron Lett. 1985, 26, 4523. (b) W. Ando and T. Tsumuraya, Tetrahedron Lett. 1986, 27, 3251. (c) W. Ando, T. Tsumuraya, and M. Goto, Tetrahedron Lett. 1986, 27, 5105.

127.(a) T. Tsumuraya, S. Sato, and W. Ando, Organometallics 1989, 8, 161. (b) W. Ando and T. Tsumuraya, Organometallics 1989, 8, 1467.

128.M. Denk, R. Lennon, R. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner, and N. Metzler, J. Am. Chem. Soc. 1994, 116, 2691.

712SILYLENES (AND GERMYLENES, STANNYLENES, PLUMBYLENES)

129.For reviews of stable diaminosilylenes, see (a) R. West and M. Denk, Pure Appl. Chem. 1996, 68, 785. (b) M. Denk, R. West, R. Hayashi, Y. Apeloig, R. Pauncz, and M. Karni, in Organosilicon Chemistry II, (Eds. N. Auner and J. Weis), VCH, Weinheim, 1996, 251.

(c) B. Gehrhus and M. F. Lappert, Phosphorus, Sulfur Silicon Relat. Elem. 1997, 124,

125, 537. See also, Ref. 1q.

130.(a) M. Denk, J. C. Green, N. Metzler, and M. Wagner, J. Chem. Soc., Dalton Trans. 1994, 2405. (b) B. Gehrhus, M. F. Lappert, J. Heinicke, R. Boese, and D. Bla´ser, J. Chem. Soc., Chem. Commun. 1995, 1931. (c) J. Heinicke, A. Opera, M. K. Kindermann, T. Karbati, and L. Nyula´szi, Chem. Eur. J. 1998, 4, 541.

131.M. Haaf, A. Schmiedl, T. A. Schmedake, D. R. Powell, A. J. Millevolte, M. Denk, and R. West, J. Am. Chem. Soc. 1998, 120, 12714.

132.B. Gehrhus, P. B. Hitchcock, and M. F. Lappert, Organometallics 1997, 16, 4861

133.B. Gehrhus and M. F. Lappert, Phosphorus, Sulfur, Silicon 1997, 125, 537.

134.For a review, see: M. F. Lappert, Main Group Metal Chem. 1994, 17, 183.

135.D. F. Moser, T. Bosse, J. Olson, J. L. Moser, I. A. Guzei, and R. West, J. Am. Chem. Soc. 2002, 124, 4186.

136.M. Kira, S. Ishida, T. Iwamoto, and C. Kabuto, J. Am. Chem. Soc. 1999, 121, 9772.

137.J. Belzner and H. Ihmels, Adv. Organometal. Chem. 1998, 43, 1.

pp.511–554.

139.M. Kira, S. Ishida, T. Iwamoto, M. Ichinohe, C. Kabuto, L. Ignatovich, and H. Sakurai,

Chem. Lett. 1999, 263.

140.M. Kira, R. Yauchibara, R. Hirano, C. Kabuto, and H. Sakurai, J. Am. Chem. Soc. 1991, 113, 7785.

141.S. Nagase and T. Kudo, J. Chem. Soc., Chem. Commun. 1984, 1392.

142.(a) S. Masamune and L. R. Sita, J. Am. Chem. Soc. 1985, 107, 6390. (b) T. Fjeldberg, A. Haaland, M. F. Lappert, B. E. R. Schilling, R. Seip, and A. J. Thorne, J. Chem. Soc., Chem. Commun. 1982, 1407. (c) J. D. Cotton, P. J. Davidson, and M. F. Lappert, J. Chem. Soc., Dalton Trans. 1976, 2275. (d) K. W. Zilm, G. A. Lawless, R. M. Merrill, J. M. Millar, and G. G. Webb, J. Am. Chem. Soc. 1987, 109, 7236.

143.N. S. Issacs, in Physical Organic Chemistry, Longman Scientific & Technical, UK, 1986,

pp.1–76.

144.(a) K. Krogh-Jespersen, J. Am. Chem. Soc. 1985, 107, 537. (b) R. S. Grev, H. F. Schaefer, III, and K. M. Baines, J. Am. Chem. Soc. 1992, 112, 9458.

145.(a) D. E. Goldberg, P. B. Hitchcock, M. F. Lappert, K. M. Thomas, A. J. Thorne, T. Fjeldberg, A. Haaland, and B. E. R. Schilling, J. Chem. Soc., Dalton Trans. 1986, 2387.

(b)G. Trinquier, J.-P. Marliew, and P. Rivie´re, J. Am. Chem. Soc. 1982, 104, 4529.

146.A. Ma´rquez, G. G. Gonza`lez, and J. F. Sanz, Chem. Phys. 1989, 138, 99.

147.(a) N. Tokitoh, H. Suzuki, R. Okazaki, and K. Ogawa, J. Am. Chem. Soc. 1993, 115, 10428. (b) H. Suzuki, N. Tokitoh, R. Okazaki, J. Harada, K. Ogawa, S. Tomoda, and M. Goto, Organometallics 1995, 14, 1016. (c) H. Suzuki, N. Tokitoh, and R. Okazaki, Bull. Chem. Soc. Jpn. 1995, 68, 2471.

148.H. Suzuki, N. Tokitoh, and R. Okazaki, J. Am. Chem. Soc. 1994, 116, 11572.

149.N. Tokitoh, H. Suzuki, and R. Okazaki, Chem. Commun. 1996, 124.

REFERENCES 713

150.N. Tokitoh, H. Suzuki, N. Takeda, T. Kajiwara, T. Sasamori, and R. Okazaki, Silicon Chemistry, in press.

151.N. Takeda, H. Suzuki, N. Tokitoh, R. Okazaki, and S. Nagase, J. Am. Chem. Soc. 1997, 119, 1456.

152.H. Spitzner and R. West, unpublished results.

153.J. Hermanns and B. Schmidt, J. Chem. Soc., Perkin Trans. 1 1998, 2209.

154.(a) M. Ishikawa, F. Ohi, and M. Kumada, J. Organometal. Chem. 1975, 86, C23. (b) M. Ishikawa, K. Nakagawa, and M. Kumada, J. Organometal. Chem. 1979, 178, 105. (c) P. P. Gaspar and R.-J. Hwang, J. Am. Chem. Soc. 1974, 96, 6198. (d) H. Sakurai, Y. Kobayashi, R. Sato, and Y. Nakadaira, Chem. Lett. 1983, 1197. (e) D. Lei, R.-J. Hwang, and P. P. Gaspar, J. Organometal. Chem. 1984, 271. (f) D. Lei and P. P. Gaspar, Res. Chem. Intermed. 1983, 12, 103. (g) K. L. Bobbitt and P. P. Gaspar, J. Organometal. Chem. 1995, 499, 17.

155.(a) S. Zhang and R. T. Conlin, J. Am. Chem. Soc. 1991, 113, 4272. (b) M. Weidenbruch, E. Kroke, H. Marsmann, S. Pohl, and W. Saak, J. Chem. Soc., Chem. Commun. 1994, 1233. (c) E. Kroke, S. Willms, M. Weidenbruch, W. Saak, S. Pohl, and H. Marsmann,

Tetrahedron Lett. 1996, 37, 3675.

156.(a) N. Takeda, N. Tokitoh, and R. Okazaki, Chem. Lett. 2000, 622. (b) N. Takeda, T. Kajiwara, H. Suzuki, R. Okazaki, and N. Tokitoh, Chem. Eur. J., in press.

157.P. J. Davidson, D. H. Harris, and M. F. Lappert, J. Chem. Soc., Dalton Trans. 1977, 2268.

158.P. Jutzi, A. Becker, H. G. Stammler, and B. Neumann, Organometallics 1991, 10, 1647.

159.J. Bender, IV., M. M. B. Holl, and J. W. Kamp, Organometallics 1997, 16, 2743.

160.P. Jutzi, H. Schmidt, B. Neumann, and H. G. Stammler, Organometallics 1996, 15, 741.

161.R. S. Simons, L. Pu, M. M. Olmstead, and P. P. Power, Organometallics 1997, 16, 1920.

162.L. Lange, B. Meyer, and W.-W. du Mont, J. Organometal. Chem. 1987, 329, C17.

163.N. Tokitoh, K. Kishikawa, and R. Okazaki, J. Chem. Soc., Chem. Commun. 1995, 1425.

164.(a) N. Tokitoh, T. Matsumoto, K. Manmaru, and R. Okazaki, J. Am. Chem. Soc. 1993, 115, 8855. (b) N. Tokitoh, K. Manmaru, and R. Okazaki, Organometallics 1994, 13, 167.

(c) N. Tokitoh, K. Manmaru, and R. Okazaki, Nippon Kagaku Kai Shi 1994, 240. (d) N. Tokitoh, K. Kishikawa, T. Matsumoto, and R. Okazaki, Chem. Lett. 1995, 827.

165.T. Matsumoto, N. Tokitoh, and R. Okazaki, J. Am. Chem. Soc. 1999, 121, 8811.

166.N. Tokitoh, T. Matsumoto, and R. Okazaki, Bull. Chem. Soc. Jpn. 1999, 72, 1665.

167.N. Tokitoh, T. Matsumoto, and R. Okazaki, J. Am. Chem. Soc. 1997, 119, 2337.

168.K. Kishikawa, N. Tokitoh, and R. Okazaki, Chem. Lett. 1998, 239.

169.N. Tokitoh, K. Kishikawa, R. Okazaki, T. Sasamori, N. Nakata, and N. Takeda,

Polyhedron 2002, 21, 563.

170.H. Spitzner and R. West, unpublished results. For the synthesis of compound [(Me3Si)2CH]2Si Si[CH(SiMe3)2]2, see: S. Masamune, Y. Eriyama, and T. Kawase,

Angew. Chem., Int. Ed. Engl. 1987, 26, 584.

171.T. Matsumoto, N. Tokitoh, and R. Okazaki, J. Chem. Soc., Chem. Commun. 1997, 1553.

172.K. Kishikawa, N. Tokitoh, and R. Okazaki, Organometallics 1997, 16, 5127.

173.K. Kishikawa, N. Tokitoh, and R. Okazaki, Chem. Lett. 1996, 695.

174.T. Fjeldberg, H. Hope, M. F. Lappert, P. P. Power, and A. J. Thorne, J. Chem. Soc., Chem. Commun. 1983, 639.

714SILYLENES (AND GERMYLENES, STANNYLENES, PLUMBYLENES)

175.B. C¸ etinkaya, I. Gu¨mru¨kc¸u¨, M. F. Lappert, J. L. Atwood, R. D. Rodgers, and M. J. Zatorotoko, J. Am. Chem. Soc. 1980, 102, 2088.

176.P. B. Hitchcock, M. F. Lappert, B. J. Samways, and E. L. Weinberg, J. Chem. Soc., Chem. Commun. 1983, 1492.

177.L. M. Engelhardt, B. S. Jolly, M. F. Lappert, C. L. Laston, and A. H. White, J. Chem. Soc., Chem. Commun. 1988, 336.

178.(a) H. Gru¨tzmacher, H. Pritzkow, and F. T. Edelmann, Organometallics 1991, 10, 23.

(b)M. P. Bigwood, J. Corvan, and J. J. Zuckermann, J. Am. Chem. Soc. 1981, 103, 7643.

179.(a) D. E. Goldberg, D. H. Harris, M. F. Lappert, and K. M. Thomas, J. Chem. Soc., Chem. Commun. 1976, 261. (b) J. D. Cotton, P. J. Davidson, M. F. Lappert, and J. D. Donaldson,

J. Chem. Soc., Dalton Trans. 1976, 2286.

180.M. Weidenbruch, J. Schlaefke, A. Scha¨fer, K. Peters, H. v. G. Schnering, and H. Marsmann, Angew. Chem., Int. Ed. Engl. 1994, 33, 1846.

181.(a) N. Tokitoh, M. Saito, and R. Okazaki, J. Am. Chem. Soc. 1993, 115, 2065. (b) M. Saito, N. Tokitoh, and R. Okazaki, Organometallics 1996, 15, 4531.

182.M. Saito, N. Tokitoh, and R. Okazaki, Chem. Lett. 1996, 265.

183.For reviews, see: (a) P. Rivie`re, M. Rivie´re-Baudet, and J. Satge´, in Comprehensive Organometallic Chemistry, Vol. 2, Pergamon, New York, 1982, p. 670. (b) P. G. Harison, in Comprehensive Organometallic Chemistry II, Vol. 2, Pergamon, New York, 1995, p. 305. (c) P. G. Harrison, in Comprehensive Coordination Chemistry, Vol. 3, Pergamon, Oxford, UK, 1987, p. 185. (d) E. W. Abel, in Comprehensive Inorganic Chemistry, Vol. 2, Pergamon, Oxford, UK, 1973, p. 105.

184.E. O. Fischer and H. Grubert, Z. Anorg. Allg. Chem. 1956, 286, 237.

185.(a) D. H. Harris and M. F. Lappert, J. Chem. Soc., Chem. Commun. 1974, 895. (b) M. J. S. Gyane, D. H. Harris, M. F. Lappert, P. P. Power, P. Rivie´re, M. Rivie´re-Baudet, J. Chem. Soc., Dalton Trans. 1977, 2004.

186.(a) N. Kano, N. Tokitoh, and R. Okazaki, Organometallics 1997, 16, 4237. (b) K. Kano, N. Tokitoh, and R. Okazaki, Phosphorus, Sulfur, Silicon, Related Elem. 1997, 124–125, 517.

187.S. Brooker, J.-K. Buijink, and F. T. Edelmann, Organometallics 1991, 10, 25.

188.(a) C. Drost, P. B. Hitchcock, M. F. Lappert, and L. J.-M. Pierseens, J. Chem. Soc., Chem. Commun. 1997, 1141. (b) P. B. Hitchcock, M. F. Lappert, and Z.-X. Wang, J. Chem. Soc., Chem. Commun. 1997, 1113. (c) W.-P. Leung, W.-H. Kwok, L.-H. Weng, L. T. Low, Z. Y. Zhou, and T. C. Mak, J. Chem. Soc., Dalton Trans. 1997, 4301.

189.M. Stu¨rmann, M. Weidenbruch, K. W. Klinkhammer, F. Lissner, and H. Marsmann,

Organometallics 1998, 17, 4425.

190.(a) P. J. Davidson and M. F. Lappert, J. Chem. Soc., Chem. Commun. 1973, 317. (b) J. D. Cotton, P. J. Davidson, D. E. Goldberg, M. F. Lappert, and K. M. Thomas, J. Chem. Soc., Chem. Commun. 1974, 893.

191.K. W. Klinkhammer, unpublished results.

192.C. Eaborn, T. Ganicz, P. B. Hitchcock, J. D. Smith, and S. E. So¨zerli, Organometallics 1997, 16, 5621.

193.C. Kano, N. Tokitoh, and R. Okazaki, Organometallics 1997, 16, 2748.

194.(a) N. Kano, K. Shibata, N. Tokitoh, and R. Okazaki, Organometallics 1999, 18, 2999.

(b)N. Kano, N. Tokitoh, and R. Okazaki, J. Synth. Org. Chem. Jpn. (Yuki Gosei Kagaku Kyokai Shi) 1998, 56, 919.

REFERENCES 715

195.C. Glidewell, J. Organometal. Chem. 1990, 398, 241.

196.K. W. Klinkhammer, T. F. Fa¨ssler, and H. Gru¨tzmacher, Angew. Chem. Int. Ed. Engl. 1998, 37, 124.

197.(a) G. Trinquier and J.-P. Marlieu, J. Am. Chem. Soc. 1987, 109, 5303. (b) G. Trinquier,

J.Am. Chem. Soc. 1990, 112, 2130. (c) H. Jacobsen and T. Ziegler, J. Am. Chem. Soc. 1994, 116, 3667.

198.M. Stu¨rmann, W. Saak, H. Marsmann, and M. Weidenbruch, Angew. Chem. Int. Ed. Engl. 1999, 38, 187.

199.(a) M. Stu¨rmann, W. Saak, and M. Weidenbruch, Z. Anorg. Alleg. Chem. 1999, 625, 705.

(b) M. Stu¨rmann, W. Saak, M. Weidenbruch, and K. W. Klinkhammer, Eur. J. Inorg. Chem. 1999, 579.

200.(a) N. Tokitoh, N. Kano, K. Shibata, and R. Okazaki, Organometallics 1995, 14, 3121.

(b) N. Kano, N. Tokitoh, and R. Okazaki, Chem. Lett. 1997, 277.

201.(a) H. Suzuki, N. Tokitoh, S. Nagase, and R. Okazaki, J. Am. Chem. Soc. 1994, 116, 11578. (b) H. Suzuki, N. Tokitoh, R. Okazaki, S. Nagase, and M. Goto, J. Am. Chem. Soc. 1998, 120, 11096.

202.M. Saito, N. Tokitoh, and R. Okazaki, J. Am. Chem. Soc. 1997, 119, 11124.

203.S. Nagase, unpublished results. See also, Ref. 194b.

204.For the calculation on R2M O systems, see: J. Kapp, M. Remko, and P. v. R. Schleyer,

J.Am. Chem. Soc. 1996, 118, 5745.

205.N. Kano, N. Tokitoh, and R. Okazaki, Organometallics 1998, 17, 1241.

206.M. Saito, N. Tokitoh, and R. Okazaki, Organometallics 1995, 14, 3620.