109918-87-8Relevant 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.
