Electrophilic Addition of 4'-Nitrobenzenesulphenanilide to Alkynes in Acetic Acid. A Synthesis of Beta-Acetoxyvinyl Sulphides. J. Chem. Soc. Perkin Trans. 1, 1113, (1989).

4′-Nitrobenzenesulphenanilide reacts at room temperature with simple alkyl- and aryl-alkynes in acetic acid in the presence of boron trifluoride–diethyl ether to afford products of acetoxysulphenylation in moderate to good yields. The addition products are generally produced with trans-stereospecificity and in a regioselective fashion (Markovnikov orientation). The findings are consistent with a mechanism involving intermediary of thiirenium ions which would result from alkyne attack at the sulphur atom of the anilide complexed with boron trifluoride