Reactivite des 1-F-alkyl-2-fluoroethyl p-toluenesulphonates en milieu basique

Article abstract of DOI:10.1016/S0022-1139(00)81105-7

The simple 2-fluorotosylates eliminate p-toluenesulphonic acid (HOTs) in baisc media, the tosyl group being substituted by the action of a nucleophile.In contrast the F-alkylated homologous R_F-CHOTs-CH2F undergo elimination of HF in the presence of a donor reagent leading to the 1-F-alkylvinyl p-toluenesulphonates R_F-COTs=CH2.Depending on the reaction conditions and the nature of the base, these vinyl tosylates can react firther to give other F-alkylated products (F-alkylmethylketones, 1-hydroxy F-alkanes, 1-F-alkyl ethanols and F-alkylmethylhydrazones).