86808-93-7Relevant academic research and scientific papers
NUCLEOPHILIC REACTIONS AT A VINYL CENTER. XI. EXCHANGE IN β,β-DICHLOROVINYL SULFONES BY FLUORINE AND IODINE
Shainyan, B. A.,Mirskova, A. N.
, p. 1022 - 1026 (2007/10/02)
We studied the reaction of β,β-dichlorovinyl sulfones with potassium fluoride in dimethyl sulfoxide and dimethylformamide, and with sodium iodide in acetone.In the reaction with KF the sulfones RSO2CH2CF3 and RSO2CH3 are formed in a ratio that depends on the amount of water in the organic solvent.Organyl methyl sulfones are not formed in absolute DMSO.A mechanism was proposed for the reaction of β,β-dichlorovinyl sulfones with KF.In the reaction with NaI one chlorine atom is replaced to give the β-chloro-β-iodosulfone.The kinetics of the reactions of ethyl β,β-dichlorovinyl sulfone and ethyl β-chloro-β-iodovinyl sulfone with sodium methoxide in methanol at 0-40 deg C was studied.From a comparison of the activation parameters it follows that in the first step of the reaction of the dichlorovinyl sulfone the chlorine atom cis to the sulfo group is replaced by CH3O-, while in the first step of the reaction of the chloroiodovinyl sulfone the chlorine atom trans to the sulfo group is replaced by CH3O-.The iodine atom is replaced at a rate that is three orders of magnitude slower than that of the chlorine atom.
