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For addition to acetylenes, see: (a) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Am. Chem. Soc. 1975, 97, 931. (b) Okinoshima, H.; Yamamoto, K.; Kumada, M. J. Organomet. Chem. 1975, 86, C27. (c) Tamao, K.; Hayashi, T.; Kumada, M. J. Organomet. Chem. 1976, 114, C19. (d) Watanabe, H.; Kobayashi, M.; Higuchi, K.; Nagai, Y. J. Organomet. Chem. 1980, 186, 51. (e) Matsumoto, H.; Matsubara, I.; Kato, T.; Shono, K.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1980, 199, 43. (f) Watanabe, H.; Kobayashi, M.; Saito, M.; Nagai, Y. J. Organomet. Chem. 1981, 216, 149. (g) Yamashita, H.; Catellani, M.; Tanaka, M. Chem. Lett. 1991, 241. (h) Ito, Y.; Suginome, M.; Murakami, M. J. Org. Chem. 1991, 56, 1948. (i) Yamashita, H.; Tanaka, M. Chem. Lett. 1992, 1547. (j) Finckh, W.; Tang, B.-Z.; Lough, A.; Manners, I. Organometallics 1992, 11, 2904. (k) Murakami, M.; Oike, H.; Sugawara, M.; Suginome, M.; Ito, Y. Tetrahedron 1993, 49, 3933. (l) Murakami, M.; Suginome, M.; Fujimoto, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1473. For some recent papers on addition to other unsaturated compounds, see: (m) Ishikawa, M.; Nishimura, Y.; Sakamoto, H.; Ono, T.; Ohshita, J. Organometallics 1992, 11, 483. (n) Tsuji, Y.; Lago, R. M.; Tomohiro, S.; Tsuneishi, H. Organometallics 1992, 11, 2353. (o) Hayashi, T.; Kobayashi, T.-a.; Kawamoto, A. M.; Yamashita, H.; Tanaka, M. Organometallics 1990, 9, 280. (p) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487. (q) Ito, Y.; Suginome, M.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1991, 113, 8899. (r) Yamashita, H.; Reddy, N. P.; Tanaka, M. Chem. Lett. 1993, 315. (s) Yamashita, H.; Reddy, N. P.; Tanaka, M. Macromolecules 1993, 26, 2143.
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1,4-Disilacyclohexa-2,5-dienes are known to be formed in the reactions of thermally generated silylene species with acetylenes. For instance, see: (a) Atwell, W. H.; Weyenberg, D. R. J. Am. Chem. Soc. 1968, 90, 3438 and references cited therein. (b) Barton, T. J.; Kilgour, J. A. J. Am. Chem. Soc. 1976, 98, 7746 and references cited therein. (c) Halevi, E. A.; West, R. J. Organomet. Chem. 1982, 240, 129 and references cited therein.
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For examples of palladium-catalyzed oligo- and/or polymerization of terminal acetylenes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 15, 325. (b) Simionescu, C. I.; Percec, V.; Dumitrescu, S. J. Polym. Sci. Polym. Chem. Ed. 1977, 15, 2497. (c) Ishikawa, M.; Oshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. For examples of other transition metal-catalyzed oligo- and/ or polymerizations of 2a, see: (d) Iwashita, Y.; Tamura, F. Bull. Chem. Soc. Jpn. 1970, 43, 1517. (e) Wen, T. C.; Chang, C. C.; Chuang, Y. D.; Chiu, J. P.; Chang, C. T. J. Am. Chem. Soc. 1981, 103, 4576. (f) Matsuda, T.; Mouri, T.; Higashimura, T. Bull. Chem. Soc. Jpn. 1980, 53, 1152.
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Formation of 1,4-disilacyclohexa-2,5-dienes, presumably via silylene species, was observed in the palladium-catalyzed reactions of cyclooligosilanes with acetylenes as well (b) Ishikawa M.; Fukui, T. Chem. Express 1987, 2, 623.
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Formation of 1,4-disilacyclohexa-2,5-dienes, presumably via silylene species, was observed in the palladium-catalyzed reactions of cyclooligosilanes with acetylenes as well: (a) Carlson, C. W.; West, R. Organometallics 1983, 2, 1801. (b) Ishikawa M.; Fukui, T. Chem. Express 1987, 2, 623.
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See also: Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1992, 11, 3227.
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For other examples of oxidative addition of the Si-Si bonds of halogen-substituted noncyclic disilanes to platinum(0) or palladium-(0) complexes, see (b) Glockling, F.; Houston, R. E. J. Organomet. Chem. 1973, 50, C31. (c) Eaborn, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. (d) Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900.
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Generation of silylene species from oligosilanylmetal complexes has been increasingly documented. For examples, see and references cited therein. (b) Pannell, K. H.; Brun, M.-C.; Sharma, H.; Jones, K.; Sharma, S. Organometallics 1994, 13, 1075 and references cited therein. (c) Tamao, K.; Tarao, Y.; Nakagawa, Y.; Nagata, K.; Ito, Y. Organometallics 1993, 12, 1113
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Generation of silylene species from oligosilanylmetal complexes has been increasingly documented. For examples, see: (a) Tobita, H.; Wada, H.; Ueno, K.; Ogino, H. Organometallics 1994, 13, 2545 and references cited therein. (b) Pannell, K. H.; Brun, M.-C.; Sharma, H.; Jones, K.; Sharma, S. Organometallics 1994, 13, 1075 and references cited therein. (c) Tamao, K.; Tarao, Y.; Nakagawa, Y.; Nagata, K.; Ito, Y. Organometallics 1993, 12, 1113.
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Electronegative substituents at the silicon atoms are known to stabilize the Si-M (M = transition metal) bonds. For instance, see
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Electronegative substituents at the silicon atoms are known to stabilize the Si-M (M = transition metal) bonds. For instance, see: Aylett, B. J. Adv. Inorg. Chem. Radiochem. 1982, 25, 1.
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c in the presence of palladium catalysts. For examples of group 10 metalcatalyzed reactions, see (b) Ishikawa, M.; Sugisawa, H.; Kumada, M.; Higuchi, T.; Matsui, K.; Hirotsu, K. Organometallics 1982, 1, 1473 and references cited therein. (c) Seyferth, D.; Shannon, M. L.; Vick, S. C.; Lim, T. F. O. Organometallics 1985, 4, 57 and references cited therein
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c in the presence of palladium catalysts. For examples of group 10 metalcatalyzed reactions, see: (a) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Am. Chem. Soc. 1977, 99, 3879. (b) Ishikawa, M.; Sugisawa, H.; Kumada, M.; Higuchi, T.; Matsui, K.; Hirotsu, K. Organometallics 1982, 1, 1473 and references cited therein. (c) Seyferth, D.; Shannon, M. L.; Vick, S. C.; Lim, T. F. O. Organometallics 1985, 4, 57 and references cited therein.
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Formation of Si—C=C—Pt species by acetylene insertion into the Si—Pt bond was demonstrated in the reactions of (halogeno)Csilyl)-platinum complexes See also: (b) Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109
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Formation of Si—C=C—Pt species by acetylene insertion into the Si—Pt bond was demonstrated in the reactions of (halogeno)Csilyl)-platinum complexes: (a) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. See also: (b) Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109.
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Reductive elimination of the Si-C bond from an (alkyl)(silyl)-bis(phosphine)platinum was reported: Ozawa, F.; Hikida, T.; Hayashi, T. J. Am. Chem. Soc. 1994, 116, 2844.
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