340830-87-7Relevant articles and documents
Synthesis of monofluoroalkenes via Julia-Kocienski reaction
Prakash, G.K. Surya,Shakhmin, Anton,Zibinsky, Mikhail,Ledneczki, Istvan,Chacko, Sujith,Olah, George A.
experimental part, p. 1192 - 1197 (2011/02/22)
Monofluoromethyl 3,5-bis(trifluoromethyl)phenyl sulfone 1 was synthesized and employed in Julia-Kocienski fluoroolefination reaction with various ketones and aldehydes. Optimal reaction conditions were found to be the treatment of substrates with KOH or C
Synthesis and Horner-Wittig Chemistry of (Fluoromethyl)diphenylphosphane Oxide
Steenis, Jan Hein van,Gen, Arne van der
, p. 897 - 910 (2007/10/03)
(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 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 patern. The route presented here avoids the use of hazardous fluorohalomethanes, which were employed in several earlier Wittig-related approaches to vinyl fluorides.
