Abstract
Reactions of 1-cyano-1-methylethyl radicals produced by the decomposition of α, α'-azobisisobutyronitrile were investigated in benzenesulphonyl, ethanesulphonyl and phenylmethanesulphonyl chlorides. 1-Cyano-1-methylethyl radicals abstracted a chlorine atom from a molecule of benzensulphonyl chloride and α-cyanoisopropyl phenyl sulphone was obtained. No sulphur dioxide was detected. In ethanesulphonyl and phenylmethanesulphonyl chlorides, N-isobutyryl-α-aminoisobutyronitrile and the corresponding amide were isolated. These compounds arise apparently from hydrolysis of the keteneimine, during treatment, which is produced by combination of two 1-cyano-1-methylethyl radicals. Though phenylmethanesulphonyl chloride decomposes thermally by itself, the thermal decomposition was accelerated by addition of azobisnitrile.The reaction mechanism is discussed.
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