Are you an EPFL student looking for a semester project?
Work with us on data science and visualisation projects, and deploy your project as an app on top of Graph Search.
Concept
Tosyl group
Summary
In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula . It consists of a tolyl group, , joined to a sulfonyl group, , with the open valence on sulfur. This group is usually derived from the compound tosyl chloride, (abbreviated TsCl), which forms esters and amides of toluenesulfonic acid, (abbreviated TsOH). The para orientation illustrated (p-toluenesulfonyl) is most common, and by convention tosyl without a prefix refers to the p-toluenesulfonyl group.
The toluenesulfonate (or tosylate) group refers to the (–OTs) group, with an additional oxygen attached to sulfur and open valence on an oxygen. In a chemical name, the term tosylate may either refer to the salts containing the anion of p-toluenesulfonic acid, (e.g., sodium p-toluenesulfonate), or it may refer to esters of p-toluenesulfonic acid, TsOR (R = organyl group).
For SN2 reactions, alkyl alcohols can also be converted to alkyl tosylates, often through addition of tosyl chloride. In this reaction, the lone pair of the alcohol oxygen attacks the sulfur of the tosyl chloride, displacing the chloride and forming the tosylate with retention of reactant stereochemistry. This is useful because alcohols are poor leaving groups in SN2 reactions, in contrast to the tosylate group. It is the transformation of alkyl alcohols to alkyl tosylates that allows an SN2 reaction to occur in the presence of a good nucleophile.
A tosyl group can function as a protecting group in organic synthesis. Alcohols can be converted to tosylate groups so that they do not react. The tosylate group may later be converted back into an alcohol. The use of these functional groups is exemplified in organic synthesis of the drug tolterodine, wherein one of the steps a phenol group is protected as its tosylate and the primary alcohol as its nosylate. The latter is a leaving group for displacement by diisopropylamine:
The tosyl group is also useful as a protecting group for amines.
Official source
About this result
This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.