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A generic epoxide. In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications.
In alkanes, optimum overlap of atomic orbitals is achieved at 109.5°. The most common cyclic compounds have five or six carbons in their ring. [6] Adolf von Baeyer received a Nobel Prize in 1905 for the discovery of the Baeyer strain theory, which was an explanation of the relative stabilities of cyclic molecules in 1885.
The substituted cyclooctyne is activated for a 1,3-dipolar cycloaddition by its ring strain and electron-withdrawing fluorine substituents, which allows the reaction to take place with kinetics comparable to the Cu-catalyzed Huisgen cycloaddition. Ring strain (~18 kcal/mol) arises from the deviation of the bond angles from the ideal 180° to ...
In organic chemistry, episulfides are a class of organic compounds that contain a saturated, heterocyclic ring consisting of two carbon atoms and one sulfur atom. It is the sulfur analogue of an epoxide or aziridine. They are also known as thiiranes, olefin sulfides, thioalkylene oxides, and thiacyclopropanes. Episulfides are less common and ...
In polymer chemistry, ring-opening metathesis polymerization (ROMP) is a type of chain-growth polymerization involving olefin metathesis. [1] The reaction is driven by relieving ring strain in cyclic olefins. [2] A variety of heterogeneous and homogeneous catalysts have been developed for different polymers and mechanisms. [3]
For example, the Eubacteria strain BBSH 797 produces de-epoxidase enzymes which reduce the 12,13 carbon epoxide ring to a double bond group. [73] These, along with other microbes expressing trichothecene detoxifying properties, can be used in feed stores to prevent to toxic effect of contaminated feed upon consumption. [ 70 ]
Mitomycin C, an aziridine, is used as a chemotherapeutic agent by virtue of its antitumour activity. [1]In organic chemistry, aziridines are organic compounds containing the aziridine functional group (chemical structure (R−) 4 C 2 N−R), a three-membered heterocycle with one amine (>NR) and two methylene bridges (>CR 2).
Since epoxide is a three-membered ring molecule, it has a high degree of ring strain. Although the carbons in the ring system are tetrahedral, preferring 109.5 degrees between each atom, epoxide strains the ring angles into 60 degrees. To counter this effect, the nucleophilic aza enolates easily react with epoxides to reduce their ring strains.