180512-50-9Relevant academic research and scientific papers
Reactive dienophiles containing a difluoromethylenephosphonato group
Blades, Kevin,Lequeux, Thierry P.,Percy, Jonathan M.
, p. 1457 - 1458 (1996)
New dienophiles containing the difluoromethylenephosphonato group are synthesised from readily-available starting materials and cycloadditions with reactive dienes are executed successfully.
Synthesis of activated alkenes bearing the difluoromethylene-phosphonate group: A range of building blocks for the synthesis of secondary difluorophosphonates
Blades, Kevin,Butt, Afshan H.,Stuart Cockerill,Easterfield, Howard J.,Lequeux, Thierry P.,Percy, Jonathan M.
, p. 3609 - 3614 (2007/10/03)
Active methylene compounds reacted readily with stable hydrate 2-diethoxyphosphoryl-2,2-difluoroethane-1,1-diol to afford a range of activated alkenes bearing the difluoromethylenephosphonate group, a useful motif in the synthesis of phosphate ester mimics of biological interest. Wadsworth-Horner-Emmons reactions were employed using modified Rathke conditions for the syntheses of alkenoates, an alkenoic acid and a vinyl sulfone, while a Henry reaction followed by E1cB dehydration afforded an enedioate and a nitroalkene. A vinyl sulfoxide was less straightforward to synthesise and dephosphorylation to a difluoromethyl congener accompanied attempts to force the reaction to completion. The Royal Society of Chemistry 1999.
