68063-78-5Relevant academic research and scientific papers
Competition between Isomerization and Addition in the Sonication of Vinyl Sulfones in the Presence of Bromotrichloromethane
Peters, Dietmar,Pautet, Felix,Fakih, Hamid El,Fillion, Houda,Luche, Jean-Louis
, p. 363 - 367 (1995)
(E)- and (Z)-vinyl sulfones isomerise under ultrasound irradiation in carbon tetrachloride in the presence of bromoform or bromotrichloromethane to give an E/Z equilibrium mixture via bromine radicals.Furthermore, the bromine radicals formed add to the C=C double bond (presumably of the Z isomer) to form vic-dibromo compounds.In pure CBrCl3 this addition reaction reaches a 99percent yield.In tetrahydrofurane/CBr4 (or CBrCl3) no isomerization is observed since the bromine radicals react probably with the THF.The addition is also favoured by highly efficient energy transmission.
Synthesis of vinyl sulfones from aryl methyl ketones under sonochemical conditions and formation of allylsulfones
El Fakih,Pautet,Peters,Fillion,Luche
, p. 3225 - 3233 (2007/10/02)
An efficient synthesis of vinyl sulfones 3a-o from aryl methyl ketones 2 bearing an electron withdrawing group and the phosphonic ester 1 under sonochemical conditions is reported. These compounds are generally obtained as an E/Z mixture. Formation of the allyl sulfones 4 is also observed.
Sonochemical Wittig-Horner synthesis of vinyl sulfones from 4-nitro acetophenone as a model for enolisable ketones
El Fakih,Pautet,Fillion,Luche
, p. 4909 - 4910 (2007/10/02)
Ultrasonic irradiation permits to improve substantially the yield of the Wittig-Horner reaction between sulfonomethylphosphonate anion and 4-nitro acetophenone, taken as a model for enolisable ketones.
