Thorpe-Ingold effect

From Wikipedia, the free encyclopedia

Also gem-dimethyl effect, or angle compression.

It was first observed by Beesley, Thorpe and Ingold in 1916 when they were studying cyclization of compounds. The presence of a quaternary carbon (e.g, a gem-dimethyl group) in an alkyl chain increases rates and equilibrium constants of a cyclization reactions.

Many cyclization reactions use this methodology in order to improve the yields, as olefin metathesis, diels-alder and others.

Furstner and Langerman JOC 1996, 61 8746