Solid-phase synthesis on functionalised fluoropolymer resins. Part 1: Nafion resin sulfonamide-immobilised carboxylic acid derivatives and aryl vinyl sulfones

The preparation and properties of Nafion resin sulfonamide systems derived from methyl glycinate and from 3-hydroxyethylaniline are described. Nafion derivatisation reactions were slow and maximum achievable functionalisations were 50% of the ion exchange capacity. In aqueous solution the resin derivatives were acid and base labile but in organic solvents the systems were stable to powerful nucleophiles and to heat. An aryl vinyl sulfone derivative used in the synthesis of tertiary amines afforded very pure products.