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Effects of aromatic substituents of electrochemically generated hypervalent iodine oxidant on oxidation reactions.

  作者 Amano, Yoshiharu;Nishiyama, Shigeru;  
  选自 期刊  Heterocycles;  卷期  2008年75-8, 7/30/08;  页码  1997-2003  
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[摘要]Phenolic oxidn. of 4-hydroxyphenylpropionic acid (5) with electrochem. generated hypervalent iodine oxidant, was performed using a variety of iodobenzene derivs. Iodobenzene derivs. carrying electron-deficient arom. moieties showed oxidant activity comparable to that of bis(2,2,2-trifluoroethoxy)phenyliodine(III) 1, and better than those carrying electron-donating groups with the exception of a Me group. In our electrochem. procedure, the oxidant from 1-iodo-4-nitrobenzene was obtained as a stable solid, while other oxidants that did not ppt. from the reaction mixt., were used in situ. Conversion of the methoxyamide 7 into the corresponding azaspiro deriv. 3 was also performed by the oxidants carrying arom. substitutions.

 
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