Reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with arenethiols and alkanethiols in dimethyl sulfoxide in the presense of KOH

The reaction of 1-(alk-1-ynyl)-1-chlorocyclopropanes with arenethiols in DMSO in the presence of KOH at 90–100 °C affords the corresponding 1-(alk-1-ynyl)-2-arylsulfanyl-cyclopropanes in the yields up to 67%. At the same time, [1,2-bis(alkylsulfanylalk-1-enyl]cyclopropanes or mixtures of isomeric 1-(alk-1-ynyl)-2-alkyltsulfanylcyclopropanes and (alkylsulfanyl)alkenylidenecyclopropanes are formed in analogous reactions with alkanethiols depending on the substituent at the triple bond of the starting compound.