Abstract
Perfluoraliphatic mono- and di-Grignard reagents (R fMgX, XMgR′ fMgX) have been conveniently synthesized in excellent yields (90–100%) through metalhalogen exchange reactions. The degree of exchange has been found to be subject to a number of experimental parameters, e.g. the nature of the solvent (tetrahydrofuran vis-à-vis diethyl ether), the type of halide displaced, the organomagnesium exchange reagent and the stoichiometry. These organomagnesium reagents have sufficient thermal stability at low temperatures (−70°) to be useful as intermediates for the synthesis of a variety of compounds. Various perfluoroaliphatic Grignard reagents have been reacted with H 3O +, CO 2, (CF 3) 2CO and cyclohexanone to yield R fH, R fCO 2H, R f(CF 3) 2OH and 1-cyclo-C 6H 10(OH)R f compounds, respectively. The selection of the proper reaction conditions, i.e. solvent, temperature and reaction time, has been found to be extremely important in the preparation of derivatives of the various perfluoroaliphatic Grignard reagents.
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