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triphenylstibine : ウィキペディア英語版
triphenylstibine

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Triphenylstibine is the chemical compound with the formula Sb(C6H5)3. Abbreviated SbPh3, this colourless solid is often considered the prototypical organoantimony compound. It is used as a ligand in coordination chemistry and as a reagent in organic synthesis.
Like the related molecules triphenylphosphine and triphenylarsine, SbPh3 is pyramidal with a propeller-like arrangement of the phenyl groups. The Sb-C distances average 2.14-2.17 Å and the C-Sb-C angle are 95°.〔Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. 〕
SbPh3 was first reported in 1886, being prepared from antimony trichloride by the reaction:〔Michaelis, A.; Reese, A. "Ueber die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Achte Abhandlung Ueber aromatische Antimonverbindungen" Liebigs Annallen der Chemie volume 233, pages 39-60 (1886). .〕
:6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl
The modern method employs the Grignard reaction, using phenylmagnesium bromide and SbCl3.〔Hiers, G. S. "Triphenylstibine" Organic Syntheses, Collected Volume 1, p.550 (1941). http://www.orgsyn.org/orgsyn/pdfs/CV1P0550.pdf〕
==References==


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