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Volumn 19, Issue 12, 2000, Pages 2258-2263

Synthesis, structure, and reactions of triaryl(methyl)bismuthonium salts

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; RATE CONSTANTS; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

EID: 0033722982     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000095d     Document Type: Article
Times cited : (16)

References (50)
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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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    • note
    • Benzene was most likely formed via the Bi-C bond cleavage of 1a by a generated protonic acid.
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    • note
    • 2BiX type of structure.
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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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    • 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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    • 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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    • 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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    • note
    • When the reaction was performed for 48-72 h, the tetraphenylbismuthonium salt was formed in ca. 5-10% yield.
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    • 2.
  • 32
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    • note
    • A small amount of insoluble substance was also formed.
  • 35
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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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    • note
    • 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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    • teXsan: Crystal Structure Analysis Package; Molecular Structure Corporation: 1985 and 1992.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.