338996-18-2Relevant articles and documents
Optimized Monofluoromethylsulfonium Reagents for Fluoromethylene-Transfer Chemistry
Sperga, Arturs,Melngaile, Renate,Kazia, Armands,Belyakov, Sergey,Veliks, Janis
, p. 3196 - 3212 (2021/02/27)
An investigation of the properties and reactivity of fluoromethylsulfonium salts resulted in the redesign of the reagents for fluoromethylene transfer chemistry. The model reaction, fluorocyclopropanation of nitrostyrene, turned out to be a suitable platf
Formation of enantiomerically pure 1-Fluorovinyl and 1-fluoromethyl sulfoxides
Van Steenis, Jan Hein,Boer, Philip W. S.,Van Der Hoeven, Harald A.,Van Der Gen, Arne
, p. 911 - 918 (2007/10/03)
(Ss)-[Fluoro(p-tolylsulfinyl)methyl]diphenylphosphane oxide (2) was obtained with complete stereoselectivity from (fluoromethyl)diphenylphosphane oxide (3) and (S)-(-)-menthyl p-toluenesulfinate. 1-Fluorovinyl p-tolyl sulfoxides 1 were prepared in good yields by Horner-Wittig reaction of 2 with aldehydes, in excellent enantiomeric excess (ee). With ketones, yields were generally low. Stereoselectivity was high for aliphatic aldehydes, producing (Z) isomers, and for benzaldehydes, yielding the (E) isomers. A two-step, one-pot procedure for the conversion of 3 into 1 was also developed. Solvolysis of 2 provided the first route to enantiomerically pure (S)-1-(fluoromethyl)sulfinyl-4-methylbenzene (7).
