J. Wielgat, Z. Domagała, R. Koliński
Aug 1, 1985
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Journal
Journal of Fluorine Chemistry
Abstract
Abstract 1,3-Dihalopropanes-2 (X = Br, Cl) were reacted with sulphur tetrafluoride to give 1,3-dihalo-2,2-difluoropropanes 1 as main products (yield 60–70 %). In addition, bis(1,3-di- halo-2-fluoropropyl)ethers 2 (yield 5–20 %) and 1,2-dihalopropenes-1 3 (yield 1–3 %) were obtained. 1,3-Difluoropropanone-2 gave only products 1 and 2 . Formation of compounds 2 and 3 is interpreted in terms of a mechanism involving fluorocarbonium ions of the type (CH 2 X) 2 C + F. The occurence of fluorocarbonium ions in the above reactions was confirmed by the reaction of 1,3-dichloroacetone with sulphur tetrafluoride and benzene followed by isolation of 1,3-dichloro-2-fluoroisopropylbenzene 4 . The latter is an electrophilic substitution of benzene with fluorocarbonium ion, i.e. fluoroalkylation of benzene.