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

Abstract

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