Reactions involving fluoride ion. Part 39. Reactions of perfluorinated dienes with oxygen and sulphur nucleophiles

Abstract

The order of reactivity of perfluorinated dienes towards methanol is 3 > 21 and the process is activated by release of angle strain. The diene 1 is hydrolysed to give perfluorotetramethyl-furan and the corresponding thiophene, is obtained by an analogous process using K₂S. Hydrolysis of compounds 2 and 3 yields diketones that are strong acids. Reactions of phenols and thiophenols with 1 give aryl ethers and sulfides and difunctional nucleophiles react with 1 to give potential polymer precursors.