35. The addition of thio-compounds to olefins. Part II. Reactions of thiolacetic and mono-, di-, and tri-chlorothiolacetic acids

Abstract

Abstract Cyclohexene, 1-methylcyclohexene, dihydromyrcene, squalene, and rubber combine additively with the above named thio acids, the reactions proceeding similarly to, but more easily than, those reported earlier for thiols. The parallelism noted previously between the ease of thiol addition and the facility of proton removal from the S—H bond, as measured by acidity, not only extends to thiol acids generally, but also accords with the fact that among the latter themselves the more acid chloro-substituted compounds are the more active addenda. A reactivity order, cyclohexenes > dihydromyrcene > squalene > rubber, is again evident, but whereas this serves to make the last olefin inert towards thiols, yet thio acid adducts are readily prepared, and these are of considerable technological interest as oil- and gasoline-resistant rubbers.