The role of F-N reagent and reaction conditions on fluoro functionalisation of substituted phenols |
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| Authors: | Igor Pravst Marjan Jereb Stojan Stavber |
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| Institution: | a Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ašker?eva 5, 1000 Ljubljana, Slovenia
b Laboratory for Organic and Bioorganic Chemistry, ‘Jozef Stefan’ Institute, Jamova 39, 1000 Ljubljana, Slovenia |
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| 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 a small effect on the rate of functionalisation, while an excellent Hammett correlation with ρ+=−2.3 was determined. |
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| Keywords: | Fluorination F-N reagents Selectfluor F-TEDA-BF4 Substituted phenols Kinetics Solvent effects Substituent effects |
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