24116-73-2Relevant academic research and scientific papers
2-Diethoxyphosphoryl alcanoic acid dianions (lithium α-lithiocarboxylates) IV. A direct route to 2-fluoro-2-alkenoic acids by the Horner synthesis. Application in the field of pyrethroids
Coutrot, Ph.,Grison, C.,Sauvetre, R.
, p. 1 - 8 (2007/10/02)
2-Diethoxyphosphoryl-2-fluoroacetic acid was converted into the lithium α lithiocarboxylate dianion by treatment with n-butyllithium in hexane/tetrahydrofuran at -70 deg C.The Horner reaction between this new dianion and carbonyl compounds gave various 2-fluoro-2alkenoic acids.Application of the method to the cis,trans caronaldehyde ethyl esters led to the 2-fluoroethenyl pyrethroid derivatives (Z-cis, E-cis, Z-trans, E-trans).
Reaction du methylure de dimethylsulfoxonium avec les ester α-fluoro α-ethyleniques
Elkik, Elias,Imbeaux-Oudotte, Michele
, p. 861 - 866 (2007/10/02)
The reaction of dimethylsulfoxonium methylide with α-fluoro α-ethylenic esters: R1-CH=CF-COOR' leads to the formation of β-keto-sulfoxonium ylides 3: R1CH=CF-CO=C-H-S+(O)(CH3)2.Reaction of ylides 3 with anhydrous HCl, at room temperature, provides β-keto γ,γ-fluoro-ethylenic sulfoxonium salts, whose decomposition, at high temperatures, leads to the formation of fluorinated chloromethyl-ketones: R1-CH=CF-CO-CH2Cl, which are not available by other methods.
