Abstract
The decomposition of 3-thenoyl and 5-nitro-2-thenoyl peroxides in aromatic solvents leads to 3-thenoyloxy and 5-nitro-2-thenoyloxy radicals, which decarboxylate to some extent to 3-thienyl (I) and 5-nitro-2-thienyl (IIa) radicals, respectively. Attack of these radicals on the solvent leads to the corresponding aryl thenoates and arylthiophenes. The Gomberg reaction of 5-carbomethoxy-2-thienylamine or the silver oxide oxidation of the related thienylhydrazine leads to 5-carbomethoxy-2-thienyl radicals (IIb). A mechanism for the formation of biphenyl, formed in small quantities in the decomposition of 5-nitro-2-thenoyl peroxide in benzene, is proposed.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
22 articles.
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