86143-89-7Relevant academic research and scientific papers
NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XX. BASE-CATALYZED REARRANGEMENT OF ARYL β,β-DIBROMOVINYL SULFONES TO Z-ARYL α,β-DIBROMOVINYL SULFONES
Shainyan, B. A.,Mirskova, A. N.
, p. 224 - 229 (2007/10/02)
A series of aryl β,β-dibromovinyl sulfones XC6H4SO2CH=CBr2 were synthesized, and their rearrangement to Z-aryl α,β-dibromovinyl sulfones XC6H4SO2CBr=CHBr by the action of KF.18-crown-6 in benzene was studied.The rearrangement rate increases with increase in the concentration of the base -> and with increase in the electron-withdrawing character of the substituent X and does not depend on the temperature.
NUCLEOPHILIC REACTIONS AT VINYL CENTER. VIII. SYNTHESIS AND PROPERTIES OF β,β-DIBROMOVINYL PHENYL SULFONE
Shainyan, B. A.,Mirskova, A. N.
, p. 443 - 446 (2007/10/02)
The radical reaction of tribromoethylene with thiophenol was investigated.In addition to the main product, β,β-dibromovinyl phenyl sulfide, 15-30percent (depending on the conditions) of a mixture of isomeric β-bromovinyl phenyl sulfides is formed. β,β-Dibromovinyl phenyl sulfone was obtained by the oxidation of dibromovinyl phenyl sulfide, and it readily enters into nucleophilic vinyl substitution of both bromine atoms.During comparison of its reactivity with the reactivity of the previously investigated dichlorovinyl phenyl sulfone a clearly defined "element-effect" was detected, indicating cleavage of the C-Hlg bond at the rate-determining stage.
