141402-82-6Relevant academic research and scientific papers
REACTIONS OF α- AND β-HALOSTYRENES WITH ARYLDIAZONIUM CHLORIDES AND SULFUR DIOXIDE. SYNTHESIS OF STYRYL ARYL SULFONES
Obushak, N. D.,Bilaya, E. E.,Ganushchak, N. I.
, p. 2105 - 2108 (2007/10/02)
Reaction of β-chloro- and β-bromostyrene with aryldiazonium chlorides and sulfur dioxide results in replacement of the halogen by the arylsulfonyl group to give E-styryl aryl sulfones.When this reaction is carried out with α-chlorostyrenes in a water-acetone-acetic acid medium, α-arylsulfonylacetophenones and Z-α-chlorostyryl aryl sulfones are obtained, while in aqueous acetone only the latter are formed.Z-α-Chlorostyryl aryl sulfones are also obtained with α-bromostyrene, irrespective of the solvent.In all cases, the arylsulfonyl group occupies the trans position to the phenyl group.The structures of the products could arise by an ion-radical mechanism.Arylsulfonation of α- and β-halostyrenes with ArSO2Cl in acetonitrile in the presence of CuCl gives a mixture of Z- and E-α-chlorostyryl aryl sulfones or styryl aryl sulfones respectively.
