97068-65-0Relevant academic research and scientific papers
The Preparation and Properties of some Chiral Fluoromethylphosphonates, Phosphonothioates, and Phosphonamidothioates
Hall, C. Richard,Inch, Thomas D.,Williams, Nancy E.
, p. 233 - 237 (2007/10/02)
Enantiomerically pure dialkyl di- and mono-fluoromethylphosphonates are prepared by fluorination of the unsubstituted phophonate anions.The corresponding fluoromethylphosphonothioates and thioic acids are prepared using (-)-ephedrine as a chiral template and the thioic acids are converted, via the chloridates, into the phosphoramidothioates.Treatment of O-ethyl S-methyl difluoromethylphosphonothioate with methoxide results in P-S bond cleavage with retention of configuration.In the corresponding monofluoromethylphosphonothioate and in S-methyl P-difluoromethyl-NN-dimethylphosphonamidothioate the reaction occurs with predominant inversion of configuration.Ethoxide-promoted endocyclic P-N bond cleavage in 2-difluoromethyl-1,3,2-oxazaphospholidine-2-thiones can occur with retention of configuration at phosphorus.
