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A Convenient Method for Regeneration of Free Thiol from a tert-Butyl Thioether

Douglas B. Grotjahn, Elijah J. Kragulj, Jeffery L. Gustafson

Abstract

When dimethylmethylthiosulfonium triflate (DMTST) is added to a tert-butyl-protected thiol (RSt-Bu), the unsymmetrical disulfide RSSMe is formed. At this point the free thiol (RSH) can be obtained by the addition of trimethylphosphine and water. Most byproducts are small organic molecules that are easily removed.

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Key concepts: Chemistry, Thioether, Thiol, Trifluoromethanesulfonate, Trimethylphosphine, Disulfide bond, Organic chemistry, Molecule