Chugaev elimination

Chugaev elimination
Origin of the name	Lev Chugaev
Kind	Elimination reaction
Identification information
RSC ontology ID	RXNO: 0000538

Chugaev elimination (Chugaev だつり, Chugaev elimination) is a reaction to pyrolize O-alkyl xanthate with kind of the elimination reaction in the organic chemistry, and to get alkene. Or it is a dehydration reaction to get alkene from first class alcohol as a key by the reaction (lower expression). This name is associated with Russian chemist, lev アレクサンドロヴィチ Chugaev (Lev Aleksandrovich Chugaev, from 1873 to 1922) [¹].

At first O-alkyl xanthic acid anion is enacted when I trigger carbon disulfide to alkoxide which I produced with a base from alcohol. I let iodomethane coexist then and assume it S-methyl ester.

A concerted syn elimination happens like a lower expression, and alkene is provided when I heat this ester to around 200 degrees Celsius. Through a transition state of the 6-membered ring form, hydrogen atoms on β-carbon transpose 1,5-to the sulfur top. The ester to by-produce with alkene disintegrates successively to sulfuration carbonyl (O=C=S) and methanethiol (CH₃SH).

References

• Latscha, H. P., Chemie-Basiswissen., Berlin(2002): Springer.

1. ^ Chugaev, L. Ber. Dtsch. Chem. Ges. 1899, 32, 3332.

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