Synlett

A convenient method for regeneration of free thiol from a tert-butyl thioether

EJ Kragulj, JL Gustafson, DB Grotjahn

Index: Kragulj, Elijah J.; Gustafson, Jeffery L.; Grotjahn, Douglas B. Synlett, 2007 , # 18 p. 2851 - 2854

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Citation Number: 2

Abstract

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.

~83%

Concave Reagents, 71) Concave Benzoic Acids

[Luening, Ulrich; Wangnick, Carsten; Peters, Karl; Schnering, Hans Georg von Chemische Berichte, 1991 , vol. 124, # 2 p. 397 - 402]

Synthesis of polyfluoroaryl [2.2] cyclophanes

[Filler,R.; Cantrell,G.L.; Wolanin,D. Journal of Fluorine Chemistry, 1986 , vol. 30, p. 399]

Concave Reagents, 71) Concave Benzoic Acids

[Luening, Ulrich; Wangnick, Carsten; Peters, Karl; Schnering, Hans Georg von Chemische Berichte, 1991 , vol. 124, # 2 p. 397 - 402]

Analogs of 2, 6-Pyridinedimethanol Bis (N-methylcarbamate)

[Juby,P.F. et al. Journal of Medicinal Chemistry, 1967 , vol. 10, p. 491 - 495]