183204-00-4Relevant academic research and scientific papers
Preparation of new wittig reagents and their application to the synthesis of α,β-unsaturated phosphonates
Xu, Yibo,Flavin, Michael T.,Xu, Ze-Qi
, p. 7697 - 7701 (2007/10/03)
The Wittig reagent [(diethoxyphosphinyl)methylidene]triphenylphosphorane (1b) has been successfully synthesized for the first time via its phosphonium triflate salt (4a), by treating (diethoxyphosphinyl)methyl triflate with triphenylphosphine. The procedure has been applied to the synthesis of other phosphoranes and phosphonium salts. The new Wittig reagents thus synthesized were treated with various aldehydes and an activated ketone, affording the corresponding α,β-unsaturated phosphonates. Triphenylphosphorane 1b and triphenylphosphonium 4a led to both cis and trans isomers with the latter being predominant, while trans isomers were almost exclusively formed when tributyl reagents (1c and 4d) were used.
