Vn. Boiko et Gm. Shchupak, ION-RADICAL PERFLUOROALKYLATION .11. PERFLUOROALKYLATION OF THIOLS BYPERFLUOROALKYL IODIDES IN THE ABSENCE OF INITIATORS, Journal of fluorine chemistry, 69(3), 1994, pp. 207-212
Perfluoroalkylation of aliphatic, aromatic and heterocyclic thiols by
perfluoroalkyl iodides in the presence of Et(3)N appears to occur spon
taneously under daylight or the usual laboratory lighting conditions a
t 20-22 degrees C and is complete in 10-15 min to 2-3 h. An exception
to this rule are thiols with a low nucleophilicity. The reaction is ac
companied by thiol oxidation (2%-3%) and depends directly on the tempe
rature, lighting, solvent polarity and electronic properties of the pe
rfluoroalkylating agents and of the thiol substituents. At the same ti
me, formation of diaryl disulphides frequently occurs contrary to abov
e rules. The reaction mechanism is discussed.