Chugaev elimination

From Wikipedia, the free encyclopedia
Jump to: navigation, search

The Chugaev elimination is a chemical reaction that involves the elimination of water from alcohols to produce alkenes. The intermediate is a xanthate. It is named for its discoverer, the Russian chemist Lev Aleksandrovich Chugaev.

Cugaevalg.png

In the first step, a potassium xanthate is formed out of the alkoxide and carbon disulfide (CS2). With iodomethane, it is transformed into a xanthate.

Chugaev2.gif

At about 200 °C, the alkene is formed by an intramolecular elimination. In a 6-membered cyclic transition state the hydrogen atom is moved from the β-C-atom to the sulfur. The side product decomposes to carbonyl sulfide (OCS) and methanethiol.

Chugaev3.gif

References[edit]

External links[edit]