Tosyl
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A tosyl group (abbreviated Ts or Tos) combines the toluene and sulfonyl functional groups. The sulfonyl group consists of a hexavalent sulfur atom double bonded to two oxygen atoms and, in the tosylate group, an aromatic ring; an alkyl substituent on the R group forms a sulfonate ester. Thus, the tosylate group is the ester of toluenesulfonic acid. The para orientation illustrated (p-toluenesulfonyl) is most common, and by convention tosyl refers to the p-toluenesulfonate ester.
A tosylate ester has only a limited shelf life if it is stored outside of a desiccator as the free tosyl is readily hydrolysed by water in the presence of light. The tosyl group is electron-withdrawing. Hence, it is an excellent leaving group.
The tosyl group is also a protecting group for alcohols, prepared by combining the alcohol with toluenesulfonyl chloride in an aprotic solvent. Toluenesulfonyl chlorides activate alcohols for nucleophilic attack or elimination (dehydration).
Similarly, the brosyl (Bs) group or brosylate is a p-bromobenzenesulfonyl group with the methyl group of toluene replaced by a bromine atom. Nosyl groups in Nosylates (Ns) are 4-nitrobenzenesulfonyl groups with a nitro group in the para position.
Applications
The use of these functional groups is examplified in an organic synthesis of the drug tolterodine, where in one of the steps a phenol group is blocked as a tosyl group and the primary alcohol as a nosyl group. The latter is a leaving group for displacement by diisopropylamine [1][1]:
References
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
