I. Pravst, S. Stavber
Dec 1, 2013
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0
Influential Citations
7
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract 4-Alkyl-substituted phenols and aromatic ethers were comparatively fluorinated with electrophilic fluorinating reagents such as cesium fluoroxysulfate (CFS), Selectfluor ™ F-TEDA-BF 4 , and Accufluor ™ NFTh in MeCN or MeOH. Reactions resulted in the formation of three types of products: 2-fluoro-4-alkyl-substituted corresponding compounds ( 5 ) as a result of ortho fluorination process, 4-alkyl-4-fluoro-cyclohexa-2,5-dienone compounds ( 6 ), resulting after an addition–elimination process, and 4-fluorosubstituted corresponding compounds ( 7 ) derived from ipso attack and release of the 4-alkyl group. The distribution of products depends on the bulkiness of alkyl groups at both positions and reaction media. The reaction in methanol proved more selective toward the formation of 2-fluoro derivatives. Tyramin and l -tyrozine were transformed with NFTh reagent in methanol to their fluorophenyl-substituted derivatives in good yield.