Improvement in the synthesis of (Z)-organylthioenynes via hydrothiolation of buta-1,3-diynes: a comparative study using NaOH or TBAOH as base

Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes with sodium organylthiolate anions in reflux, generated in situ by reacting C4H9SH with NaOH, afforded (Z)-organylthioenynes in low to good yields (25-80%). By using tetrabutylammonium hydroxide (TBAOH) as base instead of NaOH, the hydrothiolation of buta-1,3-diynes was more rapid and efficient, providing (Z)-organylthioenynes in good to excellent yields (70-95%).