Related Experiment Video
Updated: Jun 3, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
[[(tert-Butyl)dimethylsilyl]oxy]methyl group for sulfur protection
Lihong Wang1, Derrick L J Clive
1Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
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.
Related Concept Videos
Preparation and Reactions of Sulfides
Structure and Nomenclature of Thiols and Sulfides
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Preparation and Reactions of Thiols
Protecting Groups for Aldehydes and Ketones: Introduction
