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

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

doi:10.1055/s-2007-991091

LETTER

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

Elijah J. Kragulj, Jeffery L. Gustafson, Douglas B. Grotjahn*
Department of Chemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA 92182-1030, USA
Fax: +1(619)5944634; e-Mail: grotjahn@sciences.sdsu.edu;

Abstract

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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.

Key words

thiol - deprotection - tert-butyl - trimethyl phosphine - thioether

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References

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