Horner-Wadsworth-Emmons olefination

What is Horner-Wadsworth-Emmons olefination?

Horner-Wadsworth-Emmons olefination is a chemical reaction used in organic synthesis to synthesize new organic compounds containing a carbon-carbon double bond (olefin). It was developed in the 1950s by American chemists J. W. Horner, J. M. Wadsworth, and Paul Emmons and is used to synthesize a variety of olefinic compounds, including unsaturated esters, amides, and carboxylic acids..

In the Horner-Wadsworth-Emmons olefination reaction, a compound containing a phosphorus-carbon double bond, such as a phosphonate ester or a phosphonate amide, is reacted with an organolithium compound in the presence of a Lewis acid catalyst. The reaction proceeds through a series of steps, including the formation of an intermediate compound called a lithium enolphosphonate. The lithium enolphosphonate is then hydrolyzed to the final product, an olefinic compound..

One of the key advantages of the Horner-Wadsworth-Emmons olefination is its high yield and good selectivity. It is also a relatively simple reaction that can be carried out under mild conditions. However, it does require the use of organolithium compounds, which can be hazardous and must be handled with care..

Horner-Wadsworth-Emmons olefination has a wide range of applications in the synthesis of a variety of olefinic compounds, including pharmaceuticals, agrochemicals, and other fine chemicals. It has also been used in the synthesis of polymers and materials for electronic applications..

Summary

Horner-Wadsworth-Emmons olefination is a valuable tool for the synthesis of olefinic compounds and has had a significant impact on the field of organic synthesis. It continues to be widely used in the synthesis of a variety of organic compounds..

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