Journal fur Praktische Chemie - Chemiker-Zeitung p. 363 - 367 (1995)
Update date:2022-08-04
Topics:
Peters, Dietmar
Pautet, Felix
Fakih, Hamid El
Fillion, Houda
Luche, Jean-Louis
(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.
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