AskDefine | Define epoxide

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English

Noun

  1. Any of a class of organic compound, cyclic ethers, having a three-membered ring; they are prepared by the selective oxidation of alkenes or by ring-closure of halohydrins; used to make plastics.

Translations

any cyclic ether, having a three-membered ring
  • Italian: epossido

Synonyms

Extensive Definition

An epoxide is a cyclic ether with only three ring atoms. This ring approximately is an equilateral triangle, i.e. its bond angles are about 60°, which makes it highly strained. The strained ring makes epoxides more reactive than other ethers, especially towards nucleophiles. Simple epoxides are named from the parent compound ethylene oxide or oxirane, such as in chloromethyloxirane. As a functional group epoxides obtain the epoxy prefix such as in the compound 1,2-epoxycycloheptane which can also be called cycloheptene epoxide.
A polymer containing unreacted epoxide units is called a polyepoxide or an epoxy. Epoxy resins are used as adhesives and structural materials. Polymerization of an epoxide gives a polyether, for example ethylene oxide polymerizes to give polyethylene glycol, also known as polyethylene oxide.

Synthesis

Epoxides are usually created by one of the following reactions:

Olefin peroxidation

Olefin peroxidation, also known as the Prilezhaev reaction involves the oxidation of an alkene with a peroxide, usually a peroxyacid like m-CPBA or with a dioxirane like DMDO. An example is the epoxidation of styrene with perbenzoic acid to styrene oxide:
The reaction proceeds via what is commonly known as the Butterfly Mechanism. It is easiest to consider the oxygen to be an electrophile, and the alkene a nucleophile, although they both operate in that capacity, and the reaction is considered to be concerted (the numbers in the mechanism below are for simplification).
Related processes include some catalytic enantioselective reactions, such as the:

Intramolecular SN2 substitution

This method is a variant of the Williamson ether synthesis. In this case, the alkoxide ion and the halide are right next to each other in the same molecule (such compounds are generically called halohydrins), which makes this a simple ring closure reaction. For example, with 2-chloropropanol:

Johnson-Corey-Chaykovsky reaction

In the Johnson-Corey-Chaykovsky reaction epoxides are generated from carbonyl groups and sulfonium ylides.

Reactions

Typical epoxide reactions are listed below.
  • Under acidic conditions, the nucleophile attacks the carbon that will form the most stable carbocation, i.e. the most substituted carbon (similar to a halonium ion). Under basic conditions, the nucleophile attacks the least substituted carbon, in accordance with standard SN2 nuclephilic addition reaction process.

See also

References

epoxide in German: Epoxide
epoxide in Spanish: Epóxido
epoxide in French: Époxyde
epoxide in Italian: Epossidi
epoxide in Macedonian: Епоксид
epoxide in Dutch: Epoxide
epoxide in Japanese: エポキシド
epoxide in Polish: Epitlenki
epoxide in Portuguese: Epóxido
epoxide in Swedish: Epoxid
epoxide in Chinese: 环氧化合物
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