1998年8月
Water-soluble non-ionic triarylbismuthanes. First synthesis and properties
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
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- 巻
- 号
- 16
- 開始ページ
- 2511
- 終了ページ
- 2517
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1039/A803946A
- 出版者・発行元
- ROYAL SOC CHEMISTRY
The synthesis and properties of some new water-soluble non-ionic triarylbismuthanes are described. o-, m- and p-Tris(methoxymethoxyphenyl)bismuthanes 1a-c are prepared from BiCl3 and the corresponding organolithium or Grignard reagents. Oxidative chlorination of 1a-c with SO2Cl2 affords tris(methoxymethoxyphenyl)bismuth dichlorides 2a-c, which are deprotected by aqueous HCl to give tris(hydroxyphenyl)bismuth dichlorides 3a-c. Treatment of tris(3-hydroxyphenyl)bismuth dichloride 3b with NH2NH2 yields tris(3-hydroxyphenyl)bismuthane 5, which dissolves in dilute aqueous NaOH. N,N-Bis(2-tert-butyl-dimethylsiloxyethyl)benzenesulfonainide, prepared from benzenesulfonyl chloride and silyl-protected diethanolamine, is ortho-lithiated and reacted with 1/3 equiv. of BiCl3 to give Ar3Bi 9a {Ar = 2-[N,N-bis-(2-tert-butyldimethylsiloxyethyl)sulfamoyl]phenyl}. m-Phenylene-bridged Bi-2- and Bi-3-polybismuthanes 12 and 13 are prepared by the reaction between ortho-lithiated 9a and Ar2BiI 10, Desilylation of 9a, 12 and 13 by Bu4NF or p-TsOH . H2O in EtOH leads to the corresponding bismuthanepolyols 11, 14 and 15, The reaction between benzene-1,3-disulfonamide 16 bearing the silyl-protected bis(2-hydroxyethyl)amino side chains and 1/3 equiv. of BiCl3 affords tris{2,4-bis[N,N-bis(2-tert-butyldimethylsiloxyethyl)sulfamoyl]phenyl}bismuthane 17, which is deprotected by p-TsOH . H2O to yield tris{2,4-bis[N,N-bis(2-hydroxyethyl)sulfamoyl]phenyl}bismuthane 18, Compounds 11, 14 and 15 are only slightly soluble in water, but compound 18 is fairly soluble.
- リンク情報
- ID情報
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- DOI : 10.1039/A803946A
- ISSN : 0300-922X
- Web of Science ID : WOS:000075664000010