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.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
