166967-44-8Relevant articles and documents
Water-soluble non-ionic triarylbismuthanes. First synthesis and properties
Matano, Yoshihiro,Aratani, Yoshiyuki,Miyamatsu, Takashi,Kurata, Haruto,Miyaji, Katsuaki,Sasako, Shigetada,Suzuki, Hitomi
, p. 2511 - 2517 (2007/10/03)
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-butyldimethylsiloxyethyl)benzenesulfonamide, 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 Bi2- and Bi3-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.
