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Arbuzov et al. postulated the formation of an intermediary methyltriphenylbismuth cation in the reaction between triphenylbismuthine and a sulfonium ylide. However, their attempt to isolate a methyltriphenylbismuthonium salt was not successful. Arbuzov, B. A.; Belkin, Y. V.; Polezhaeva, N. A.; Buslaeva, G. E. Izv. Akad. Nauk SSSR 1978, 1643.
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Henry, M. C.; Wittig, G. J. Am. Chem. Soc. 1960, 82, 563. The authors reported that triphenylbismuthine reacts with the oxonium salt but does not produce a bismuthonium salt. They also reported that triphenylstibine reacts readily with the same oxonium salt to yield methyltriphenylstibonium tetrafluoroborate.
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12944270459
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note
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Benzene was most likely formed via the Bi-C bond cleavage of 1a by a generated protonic acid.
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22
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12944270458
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note
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2BiX type of structure.
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23
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12944268404
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Parris, G. E.; Long, G. G.; Andrews, B. C.; Parris, R. M. J. Org. Chem. 1976, 41, 1276.
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24
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37049110202
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For example, see: (a) Carty, A. J.; Taylor, N. J.; Coleman, A. W.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1979, 639. (b) Godfrey, S. M.; McAuliffe, C. A.; Mackie, A. G.; Pritchard, R. G. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998; Chapter 4, pp 159-205.
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Carty, A.J.1
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0004211783
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Norman, N. C., Ed.; Blackie Academic and Professional: London, Chapter 4
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For example, see: (a) Carty, A. J.; Taylor, N. J.; Coleman, A. W.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1979, 639. (b) Godfrey, S. M.; McAuliffe, C. A.; Mackie, A. G.; Pritchard, R. G. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998; Chapter 4, pp 159-205.
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Pritchard, R.G.4
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26
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0000955279
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Recently, aryl- and alkenylboronic acids were found to be potent reagents for preparing aryl- and alkenylbismuthonium salts. (a) Matano, Y.; Begum, S. A.; Miyamatsu, T.; Suzuki, H. Organometallics 1998, 17, 4332. (b) Matano, Y.; Begum, S. A.; Miyamatsu, T.; Suzuki, H. Organometallics 1999, 18, 5668.
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27
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0001108890
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Recently, aryl- and alkenylboronic acids were found to be potent reagents for preparing aryl- and alkenylbismuthonium salts. (a) Matano, Y.; Begum, S. A.; Miyamatsu, T.; Suzuki, H. Organometallics 1998, 17, 4332. (b) Matano, Y.; Begum, S. A.; Miyamatsu, T.; Suzuki, H. Organometallics 1999, 18, 5668.
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28
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12944335191
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note
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When the reaction was performed for 48-72 h, the tetraphenylbismuthonium salt was formed in ca. 5-10% yield.
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29
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12944284691
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note
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2.
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30
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33748667285
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Suzuki, H.; Ikegami, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1997, 1609.
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0004204702
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Matano, Y.; Nomura, H.; Shiro, M.; Suzuki, H. Organometallics 1999, 18, 2580.
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34
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12944249410
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note
-
A small amount of insoluble substance was also formed.
-
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-
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35
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12944314974
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note
-
Unidentified trace components in the reaction mixture might cause disproportionation of 1a,b to 1e,f. It is likely that 4a,b transfer the methyl group to these unsymmetrical bismuthines 1e,f to afford 4e,f.
-
-
-
-
37
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12944250948
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note
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Due to the high water-solubility, methyl formate and the ammonium salt could not be recovered in the reactions with sodium aulfinate and benzoate.
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12944259106
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Casadei, M. A.; Rienzo, B. D.; Moracci, F. M. Synth. Commun. 1983, 13, 753.
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12944260605
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