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The radical-type diaddition of simple aliphatic and aromatic thiols, thiolacetic acid, dialkyldithiophosphoric (phosphorodithioic) acids, 2-mercaptoethanol, mercaptoacetic acid, 2-mercaptopropionic acid, and their esters to allene was studied. In general, such diadditions were found to be better than known metathetical reactions for the large-scale synthesis of trimethylene bis-sulfide compounds, the products of terminal diaddition. The various types of thiol compounds differ widely in their reactivity towards allene. A comparison of the data for t-butane- and benzene-thiol addition suggests that, in general, the amount of branched diadducts from monoadditions is directly proportional to the hydrogen-donor ability of the thiol, and that the amount of the allylic monoadduct formed is proportional to the stability of the thiyl radical.

Allene chemistry. VIII. Diaddition of thiol compounds to allene