Redox-transfer. Part VII. Addition of ethylene and butadiene to functionally substituted aromatic sulphonyl chlorides

Abstract

Application of the copper chloride-catalysed addition of substituted aromatic sulphonyl chlorides to ethylene and butadiene is extended to sulphonyl chlorides carrying bromine, carboxy-, chloromethyl, chlorosulphonyl, and 2-chloroethylsulphonyl substituents. Several ethylene adducts are further transformed by chlorosulphonation, dehydrochlorination, and oxidation of a methyl to a carboxy-group.

The cis–trans-isomerisation of but-2-ene by toluene-p-sulphonyl chloride at 100° is discussed. The isomerisation has a radical-chain character, is strongly retarded by chloride ions, and is completely inhibited by norbornadiene.