Radical arylation of thiobenzanilides by aryldiazonium salts in the presence of ferrocene
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.
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.
S-Arylisothiobenzanilides containing electron-withdrawing substituents on the aniline ring undergo hydrolysis under the reaction conditions.
KeywordsHydrolysis Phenyl Aniline Ferrocene Radical Chain
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