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Tosyl group (blue) with a generic "R" group attached Tosylate group with a generic "R" group attached. Note the extra oxygen, compared to plain tosyl. In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos [nb 1]) is a univalent functional group with the chemical formula −SO 2 −C 6 H 4 −CH 3.
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert -butyl ether on the phenol group.
In a famous and illustrative use of tosylate as a leaving group, the 2-norbornyl cation was formed by an elimination reaction of 7-norbornenyl tosylate. The elimination occurs 10 11 times faster than the solvolysis of anti-7-norbornyl p-toluenesulfonate. [10] Tosylates are also protecting groups for alcohols.
Thus, tosylation followed by reduction allows for removal of a hydroxyl group. Likewise, TsCl is used to prepare sulfonamides from amines: [3] CH 3 C 6 H 4 SO 2 Cl + R 2 NH → CH 3 C 6 H 4 SO 2 NR 2 + HCl. The resulting sulfonamides are non-basic and, when derived from primary amines, are even acidic. TsCl reacts with hydrazine to give p ...
Tosyl group; This page is a redirect. ... When appropriate, protection levels are automatically sensed, described and categorized. Retrieved from "https: ...
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In organic synthesis, PPTS is used as a weakly acidic catalyst, providing an organic soluble source of pyridinium (C 5 H 5 NH +) ions.For example, PPTS is used to deprotect silyl ethers or tetrahydropyranyl ethers when a substrate is unstable to stronger acid catalysts.
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