Push-pull olefin

Push-pull olefin

A push-pull olefin is a type of olefin characterized by an electron-withdrawing substituent on one side of the double bond and an electron-donating substituent on the other side. This makes the pi bond very polarized. The rotational barrier for a push-pull olefin is lower than that of an ordinary olefin and this makes it an interesting candidate for a molecular switch for instance azobenzenes. A push-pull configuration also helps to stabilize double bond because the carbon carbon bond has considerable less double bond character. For instance cyclobutadiene is a very unstable molecule but with both olefinic bonds in push-pull configuration (two ester substituents and two tertiary amine substituents) the molecule is stable indeed.

References

* "Ethyl (2-cyano-3-ethoxyacryloyl)carbamate: irreversible thermal isomerization of a push-pull olefin" Kuangsen Sung, Ming-Chi Lin, Pin-Mei Huang, Bo-Ren Zhuang, Robert Sung,Ru-Rong Wu Arkivoc 2005 p.131 [http://arkat-usa.org/ark/journal/2005/I13_General/1380/05-1380D.asp] open access publication

ee also

*Leimgruber-Batcho indole synthesis
* Application of push-pull olefins in molecular logic gates


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