[(tert-Butyl)dimethylsilyl]oxy]methyl Group for Sulfur Protection

Abstract

Aromatic and aliphatic thiols can be protected by reaction with t-BuMe(2)SiOCH(2)Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe(2)SiOCH(2)SR or t-BuMe(2)SiOCH(2)SAr are deprotected by sequential treatment with Bu(4)NF and I(2) to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined with Me(CH(2))(11)SCH(2)OSiMe(2)Bu-t and three sulfenyl chlorides.