Tetrahedron

The role of F–N reagent and reaction conditions on fluoro functionalisation of substituted phenols

I Pravst, MP Iskra, M Jereb, M Zupan, S Stavber

Index: Pravst, Igor; Iskra, Maja Papez; Jereb, Marjan; Zupan, Marko; Stavber, Stojan Tetrahedron, 2006 , vol. 62, # 18 p. 4474 - 4481

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Citation Number: 18

Abstract

The effect of steric interactions on the regioselectivity of fluorination of para alkyl substituted phenols was investigated and the strong effect of size of the alkyl substituent, the structure of the F–N reagent and the solvent on the site of fluorination was established. The course of reaction obeyed a second order rate equation, while the fluorination process required higher ΔH≠ activation than oxidation or oxidative demethylation. Solvent polarity variations had ...