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9) Miyano, S.; Tobita, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1981, 54, 3522. Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879. Wilson, J. M.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 881. Wilson, J. M.; Cram, D. J. J. Org. Chem. 1984, 49, 4930. Yamamoto, K.; Fukushima, H.; Nakazaki, M. J. Chem. Soc., Chem. Commun. 1984, 1490. Yamamoto, K.; Fukushima, H.; Yumioka, H.; Nakazaki, M. Bull. Chem. Soc. Jpn. 1985, 55, 3633. Brussee, J.; Groenedijk, J. L. G.; te Kappele. J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313. Miyano, S.; Shimizu, K.; Sato, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 1345. Meyers, A. I.; Flisak, J. R.; Aitken, R. A. J. Am. Chem. Soc. 1987, 109, 5446. Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
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Alkylation of 7 was surprisingly difficult to achieve. The reaction with a Grignard reagent afforded a very complicated mixture of unidentified products. A redistribution reaction with tetramethyltin gave mixtures of 7 and 8 ; attempts to drive the reaction to completion led to decomposition of both compounds. Likewise, among the reducing agents surveyed, only alane provided a clean product
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12) Alkylation of 7 was surprisingly difficult to achieve. The reaction with a Grignard reagent afforded a very complicated mixture of unidentified products. A redistribution reaction with tetramethyltin gave mixtures of 7 and 8 ; attempts to drive the reaction to completion led to decomposition of both compounds. Likewise, among the reducing agents surveyed, only alane provided a clean product.
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Under air the very stable radical generated from 9 can be scavenged by dioxygen molecules before hydrogen abstraction occurs; in addition, by-products containing an ethyl group were found, whose formation is probably the result of the high amounts of triethylborane used during the reaction
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15) Under air the very stable radical generated from 9 can be scavenged by dioxygen molecules before hydrogen abstraction occurs; in addition, by-products containing an ethyl group were found, whose formation is probably the result of the high amounts of triethylborane used during the reaction.
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3B see: Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041.
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119Sn-NMR spectra), the melting temperature ranges from 220 °C to 270 °C, probably because of fast decomposition of the hydride: as the fusion begins, the sample turns in a red-brown oil that slowly decomposes and becomes clear at 270 °C
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119Sn-NMR spectra), the melting temperature ranges from 220 °C to 270 °C, probably because of fast decomposition of the hydride: as the fusion begins, the sample turns in a red-brown oil that slowly decomposes and becomes clear at 270 °C.
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19) Suzuki, K.; Katayama, E.; Tsuchihashi, G. Tetrahedron Lett. 1983, 24, 4997.
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