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Chemistry · Glossary

What is Sulfonate esters?

Also known as: sulfonate ester · tosylate · mesylate

Definition 22.6 University Chemistry — Year 1 · Chapter 22 — Alcohols: Activating the OH Group

A sulfonate ester R−O−SO2−R′\mathrm{R{-}O{-}SO_2{-}R'} is formed from an alcohol and a sulfonyl chloride R′SO2Cl\mathrm{R'SO_2Cl} in the presence of a base (pyridine). The tosylate, R−OTs\ce{R-OTs}, comes from 4-methylbenzenesulfonyl chloride (tosyl chloride); the mesylate, R−OMs\ce{R-OMs}, from methanesulfonyl chloride. The sulfonate anion R′SO3−\mathrm{R'SO_3^-}, the conjugate base of a strong acid and stabilised by resonance over three oxygens, is an excellent leaving group.

Tosylation of an alcohol. The O–H bond is replaced by O–S; the C–O bond of the alcohol is not touched. Pyridine takes the HCl formed.
Tosylation of an alcohol. The O–H bond is replaced by O–S; the C–O bond of the alcohol is not touched. Pyridine takes the HCl formed.
From (S)-butan-2-ol to 2-methylbutanenitrile: the tosylation keeps the configuration, the SN2 step with cyanide inverts it. Overall: OH replaced by CN with inversion.
From (S)-butan-2-ol to 2-methylbutanenitrile: the tosylation keeps the configuration, the SN2 step with cyanide inverts it. Overall: OH replaced by CN with inversion.
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