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Abstract

Alkyne-a-sulphenic acids formed by thermolysis of w-(t-butylsu1phinyl)alkynes at 140 "C cyclized regiospecifically to 2-methylenethiacycloalkane 1 -oxides ; 2-methylenethietan 1 -oxide was not formed in this way. 2-Methylpropane-2-sulphenic acid, obtained by heating di-t-butyl sulphoxide, added regioselectively to oct-1 -yne to give predominantly 2-t-butylsulphinyloct-1 -ene, which itself decomposed thermally to a mixture of dioctenyl sulphoxides by way of alkenesulphenic acid-dialkyl sulphine interconversions. Benzenesulphenic acid, methanesulphenic acid, and ethoxycarbonylmethanesulphenic acid, conveniently generated by thermolysis of 1 -cyano-2alkyl(or aryl)sulphinylethanes, underwent intermolecular addition to unactivated and activated alkynes regioselectively to give alkenyl sulphoxides in good yields.University, Sheffield S3 7HF

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