86143-90-0Relevant academic research and scientific papers
NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XVIII. REACTIVITY OF Z-α,β-DIBROMOVINYL PHENYL SULFONE AND THE "ELEMENT EFFECT" IN α,β-DIHALOGENOVINYL SULFONES
Shainyan, B. A.,Mirskova, A. N.,Bel'skii, V. K.
, p. 1727 - 1736 (2007/10/02)
The reaction of Z-α,β-dibromovinyl phenyl sulfone PhSO2CBr=CHBr with sodium methoxide and substituted thiophenolates in methanol was investigated.With sodium methoxide the product from substitution of the bromine at the β position followed by the addition of methanol PhSO2CHBrCH(OMe)2 is formed.With sodium thiophenolates both PhSO2CBr=CHBr and other α,β-dihalogenovinyl sulfones react with substitution of both halogen atoms, leading to 1-phenylsulfonyl-1,2-bis-(arylthio)ethenes PhSO2C(SAr)=CHSAr, when a twofold excess of the nucleophile is used, but only the halogen atom at the β position is substituted when the reagents are in an equimolar ratio.The reasons for the different directions in the reaction of α,β-dihalogenovinyl sulfones with nucleophiles are considered, the kinetics of the reaction are studied, and the "element effect" is discussed.
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.
NUCLEOPHILIC REACTIONS AT VINYL CENTER. IV. REACTION OF β, β-DICHLOROVINYL SULFONES WITH SODIUM THIOPHENOLATES
Shainyan, B. A.,Mirskova, A. N.
, p. 2198 - 2203 (2007/10/02)
The kinetics of the reaction of β,β-dichlorovinyl sulfones with substituted sodium thiophenolates in methanol at 0 - 50 deg C were investigated.The reaction occurs with substitution of both chlorine atoms of thioaryl group, and the ratio of the rate constants for the substitution of the first and second chlorine atoms depends largely on the substituent in the nucleophile and depends little on the substituent in the substrate.A one-factorial and crossed analysis of the reactivity was undertaken.
