Novel Route to β-Chloro Vinyl Sulfones via the Action of Phosphorus Pentachloride on Phenacyl Aryl Sulfones in Chloroform

Abstract

Since our interest is in studying the kinetics and mechanisms of nucleophilic substitution and elimination reactions of halo olefins^1–3 so the aim of this work is to prepare compounds of the type C₆H₅CCI=CHSO₂ and to study their behaviour towards elimination and substitution reactions. Earlier preparation of these sulfones by thermal or copper-catalyzed addition of aryl sulfonyl bromides and chlorides to phenylacetylene reported a mixture of E- and Z- β-halovinyl sulfones or exclusively E-isomer^4–7. The reaction of phosphorus pentachloride with phenacyl aryl sulfones is investigated as a possible route to prepare β-chlorovinyl sulfones.