The reaction of chloro(organylthio)acetylenes with alcohols and mercaptans in the presence of their sodium derivatives
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Propanol and propylmercaptan regiospecifically add to the triple bond of chloropropylthioacetylene with attack of the nucleophile in the case of propanol at the carbon atom attached to sulfur and in the case of propylmercaptan, at the carbon atom attached to chlorine.
The addition of an alcohol occurs stereospecifically with the formation of a cis-adduct, while in the addition of propylmercaptan, cis- and trans-1,2-bis(propylthio)-2-chloroethylenes are formed.
The differences in the reaction pathways of sodium propylate and sodium propylthiolate are discussed in the framework of the effect of charge and orbital control on the reactivity of these nucleophiles.
KeywordsSodium Alcohol Sulfur Chlorine Carbon Atom
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