- Insertion of benzyne into a Bi-S bond: A new synthetic route to ortho -functionalized bismuthanes and its application to the synthesis of dibenzothiophene
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ortho-Arylthio triarylbismuthanes [2-(Ar′S)C6H 4]nBiAr3-n have been conveniently synthesized by insertion of benzyne into the bismuth-sulfur bond of (Ar′S) nBiAr3-n (n = 1, 2). A similar insertion takes place when a homologous antimony congener is used, but no reaction is observed with its phosphorus analogue. This suggests a clear difference in the bond strength between pnictogen-sulfur bonds. The carbon-bismuth bond of [2-(2-BrC 6H4S)C6H4]nBiAr 3-n undergoes Pd-catalyzed intramolecular cross-coupling to produce dibenzothiophene in good yield. An X-ray crystallographic study of 2-(2-BrC 6H4S)C6H4BiTol2 (Tol = 4-MeC6H4) reveals that this molecule is present in a dimeric structure, where the six heteroatoms including bismuth, sulfur, and bromine are linked through the nonbonded intramolecular bismuth-sulfur and intermolecular sulfur-bromine and bromine-bromine interactions.
- Chen, Jing,Murafuji, Toshihiro,Tsunashima, Ryo
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p. 4532 - 4538
(2011/11/13)
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- THE PREPARATION OF PHENYL SUBSTITUTED ANTIMONY(III) AND ANTIMONY(V) CHLORIDES AND BROMIDES
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In the absence of solvent, the redistribution of 2/1 and 1/2 molar mixtures of Ph3Sb and SbX3, where X = Cl or Br, is rapid giving quantitative yields of Ph2SbX and PhSbX2, respectively.
- Nunn, Michael,Sowerby, D. Bryan,Wesolek, Denise M.
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p. C45 - C46
(2007/10/02)
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