Although elemental sulfur (S<sub>8</sub>) is inexpensive and abundant, its insolubility in organic solvents and in water presents a challenge for its use in synthetic reactions. Here, we report the ability of 1,2-aminothiol compounds such as 1-amino-2-ethanethiol (cysteamine) or 2-aminothiophenol to accelerate the reduction of S<sub>8</sub> to form polysulfide anions and organic polysulfide compounds. In these reactions, the position of the amine moiety serves to increase the nucleophilicity of the thiol group and to stabilize thiolate-supported polysulfide moieties through hydrogen bonding. These interactions can be used to facilitate polysulfur transfer to alkenes to form organic polysulfide compounds.

1-2-Aminothiol-promoted polysulfide formation and transfer

ACS Spring 2022

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