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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.
The CH 3 C 6 H 4 SO 2 group is known as the tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH. H 2 O. [6] As with other aryl sulfonic acids, TsOH is a strong organic acid. It is about one million times stronger than benzoic acid. [6]
A tosylhydrazone in organic chemistry is a functional group with the general structure RR'C=N-NH-Ts where Ts is a tosyl group. Organic compounds having this functional group can be accessed by reaction of an aldehyde or ketone with tosylhydrazine .
As typical for Sulfonyl halides, TsCl converts alcohols (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"): CH 3 C 6 H 4 SO 2 Cl + ROH → CH 3 C 6 H 4 SO 2 OR + HCl. Tosylates can be cleaved with lithium aluminium hydride: 4 CH 3 C 6 H 4 SO 2 OR + LiAlH 4 → LiAl(O 3 SC 6 H 4 CH 3) 4 + 4 RH
Tosyl (Ts) group – Removed by concentrated acid (HBr, H 2 SO 4) & strong reducing agents (sodium in liquid ammonia or sodium naphthalenide) Other sulfonamide ( Nosyl & Nps ) groups — Removed by samarium iodide , thiophenol or other soft thiol nucleophiles, or tributyltin hydride [ 59 ]
Group name Full name Pseudoelement symbol Example Tosyl: p-toluenesulfonyl Ts Tosyl chloride (p-toluenesulfonyl chloride) CH 3 C 6 H 4 SO 2 Cl Brosyl: p-bromobenzenesulfonyl Bs Nosyl o- or p-nitrobenzenesulfonyl Ns Mesyl: methanesulfonyl Ms Mesyl chloride (methanesulfonyl chloride) CH 3 SO 2 Cl Triflyl: trifluoromethanesulfonyl Tf Tresyl: 2,2,2 ...
Tosyl group; Triflate This page was last edited on 23 January 2021, at 06:35 (UTC). Text is available under the Creative Commons Attribution-ShareAlike 4.0 License ...
A typical catalyst is (cymene)R,R-HNCHPhCHPhNTs, where Ts refers to a tosyl group (SO 2 C 6 H 4 Me) and R,R refers to the absolute configuration of the two chiral carbon centers. This work was recognized with the 2001 Nobel Prize in Chemistry to Ryōji Noyori. [5]