Radical arylation of thiobenzanilides by aryldiazonium salts in the presence of ferrocene

  • I. I. Kandror
  • I. O. Bragina
  • R. Kn. Freidlina
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Conclusions

  1. 1.

    The radical chain thiophilic arylation of thiobenzanilide and thiobenz-p-anisidide by phenyl- and p-methoxyphenyldiazonium tetrafluoroborides was carried out using ferrocene as the catalyst. The corresponding S-arylisothiobenzanilides were obtained in high yield.

     
  2. 2.

    p-Nitrophenyldiazonium tetrafluoroboride arylates these thiobenzanilides in the absence of ferrocene, presumably also by a radical mechanism; the thioamide is the catalyst for decomposition of tne aryldiazonium cation.

     
  3. 3.

    S-Arylisothiobenzanilides containing electron-withdrawing substituents on the aniline ring undergo hydrolysis under the reaction conditions.

     

Keywords

Hydrolysis Phenyl Aniline Ferrocene Radical Chain 

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Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • I. I. Kandror
    • 1
  • I. O. Bragina
    • 1
  • R. Kn. Freidlina
    • 1
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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