Synthesis and chemistry of perfluoro-2-iodo-2-methyl-alkanes

Abstract

Two novel perfluoro-tert-alkyl iodides CF3(CF2)n+1C(CF3)2I have been obtained from F-alkenes CF3(CF2)nCFC(CF3)2 (n = 0 and 1) by formal additions of iodine fluoride; these required substantial alterations of known procedure. The F-tert-alkyl iodides are the most reactive alkyl halides known so far, and they are also very toxic. The following types of reactions have been studied: (a) Nucleophilic attack of anions at the iodine, leading to F-alkenes, (b) elimination of iodine fluoride, caused by metals or metal complexes, (c) pyrolysis, to give very selectively F-isobutene and n-perfluoroalkyl iodides, (d) photolysis, and (e) thermally induced insertions into the carbon-iodine bond. Screening results on the inhalation toxicity of the iodides and of some other fluoro-compounds are also reported. © 1987.