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Volumn 14, Issue 1, 1995, Pages 530-541

Unexpected Formation of 1,4-Disilacyclohexa-2,5-dienes in the Palladium-Catalyzed Reactions of Cl(SiMe2)3Cl with Acetylenes and Its Application to Polymer Synthesis

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EID: 0001421313     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00001a072     Document Type: Article
Times cited : (61)

References (48)
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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
    • 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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    • 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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    • Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1977, 142, C45. (b) Ishikawa, M.; Sugisawa, H.; Kumada, M.; Kawakami, H.; Yamabe, T. Organometallics 1983, 2, 974. (c) Seyferth, D.; Vick, S. C.; Shannon, M. L.; Lim, T. F. O.; Duncan, D. P. J. Organomet. Chem. 1977, 135, C37 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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    • 1-Nickela-, -platina-, and -ferra-2,5-disilacyclopent-3-ene complexes are known to react with acetylenes to give 1,4-disilacyclohexa-2,5-diene compounds (b) Tanaka, M.; Uchimaru, Y. Bull. Soc. Chim. Fr. 1992, 129, 667. (c) Sakurai, H.; Kobayashi, T.; Nakadaira, Y. J. Organomet. Chem. 1978, 162, C43
    • 1-Nickela-, -platina-, and -ferra-2,5-disilacyclopent-3-ene complexes are known to react with acetylenes to give 1,4-disilacyclohexa-2,5-diene compounds: (a) Liu, C.-S.; Cheng, C.-W. J. Am. Chem. Soc. 1975, 97, 6746. (b) Tanaka, M.; Uchimaru, Y. Bull. Soc. Chim. Fr. 1992, 129, 667. (c) Sakurai, H.; Kobayashi, T.; Nakadaira, Y. J. Organomet. Chem. 1978, 162, C43.
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    • Thermally stable siloxane polymers containing 1,4-disilacyclohexa-2,5-diene rings were reported. See: Rhein, R. A. In Silicon-Based Polymer Science; Zeigler, J. M., Fearon, F. W. G., Eds.; Advances in Chemistry Series 224; American Chemical Society: Washington, DC, 1990; Chapter 19.
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