Abstract
(Fluoromethyl)diphenylphosphane oxide (1) was obtained by heating (diphenylphosphinoyl)methyl p-toluenesulfinate (2) with potassium fluoride. Compound 1 is a stable, crystalline solid, suitable for application in the Horner−Wittig reaction. The compound described in the literature under this name was found to be benzylphenylphosphinic fluoride (5). The anion of phosphane oxide 1 readily reacted with a wide range of carbonyl compounds to yield diastereomeric mixtures of α-fluoro-β-(hydroxyalkyl)phosphane oxides 7, which in most cases could be separated. The ease of phosphinate elimination to yield (E)- and (Z)-1-fluoroalkenes 8 stereoselectively was found to be strongly dependent upon conformation and substituent pattern. The route presented here avoids the use of hazardous fluorohalomethanes, which were employed in several earlier Wittig-related approaches to vinyl fluorides.
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