Redox-transfer. Part VII. Addition of ethylene and butadiene to functionally substituted aromatic sulphonyl chlorides
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1543-1545
- https://doi.org/10.1039/p19720001543
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.Keywords
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