Fluoride Ion-Induced Horner-Emmons Reaction of α-Silylalkylphosphonic Derivatives with Carbonyl Compounds

Article abstract of DOI:10.1246/bcsj.60.1831

Dimethyl α-trimethylsilylbenzylphosphonate was allowed to react with carbonyl compounds in the presence of fluoride ion to give the corresponding olefins in fairly good yields.Use of CsF in tetrahydrofuran gave the best result.On the other hand, dimethyl trimethylsilylmethylphosphonate was allowed to react similarly with benzophenone to afford 1,1-diphenylethylene, dimethyl methylphosphonate, and dimethyl 2,2-diphenylethenylphosphonate.A similar result was obtained by using O,O-diethyl trimethylsilylmethylphophonothioate.But, reaction of trimethylsilylmethylphosphonic bis(diethylamide) afforded only the protodesilylation product.