Homolytic aromatic substitution of heterocyclic compounds. Part IV. The arylation of thiophen

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Abstract
The phenylation of thiophen, carried out with several phenylating agents, afforded in each case a mixture of 2- and 3-phenylthiophens the proportions of which were in the range 90—95 : 10—5. The rates of substitution of thiophen relative to benzene by substituted phenyl radicals, generated by the aprotic diazotization of the anilines with pentyl nitrite have been found to follow, qualitatively, the order expected on the basis of the theory of polarized aryl radicals. A linear correlation has been found to hold between the partial rate factors for the 2-position of thiophen, and the substituent σ° parameters.

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