論文

査読有り 筆頭著者 責任著者
1998年8月

Water-soluble non-ionic triarylbismuthanes. First synthesis and properties

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
  • Y Matano
  • ,
  • Y Aratani
  • ,
  • T Miyamatsu
  • ,
  • H Kurata
  • ,
  • K Miyaji
  • ,
  • S Sasako
  • ,
  • H Suzuki

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
DOI
https://doi.org/10.1039/A803946A
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000075664000010&DestApp=WOS_CPL
URL
https://pubs.rsc.org/en/content/articlelanding/1998/p1/a803946a#!divAbstract
ID情報
  • DOI : 10.1039/A803946A
  • ISSN : 0300-922X
  • Web of Science ID : WOS:000075664000010

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