Epoxide

An epoxide is a cyclic ether whose three-membered ring contains two carbon atoms and one oxygen atom. Ring strain makes epoxides more reactive than ordinary ethers.

Nucleophilic ring opening: A reaction in which a nucleophile attacks a ring atom and breaks a bond, opening the ring. Nucleophiles relieve epoxide ring strain by attacking a carbon and breaking a carbon–oxygen bond.
Epoxidation: The conversion of an alkene into an epoxide by transferring an oxygen atom across its double bond. This is a direct way to prepare epoxides from alkenes.
Ether: An organic compound in which an oxygen atom is bonded to two carbon-containing groups. An epoxide is the ring-shaped, three-membered subclass of ethers.
Oxetane: A saturated four-membered heterocycle containing one oxygen atom and three carbon atoms. Its larger ring generally has less angle strain than an epoxide ring.
Acid-catalyzed ring opening: A ring-opening reaction promoted by protonation of a ring heteroatom. Protonating the epoxide oxygen makes its carbon atoms more susceptible to nucleophilic attack.
Ethylene oxide: The simplest epoxide, a volatile, reactive compound used to make industrial chemicals and sterilize equipment. This small epoxide is a major feedstock and a practical sterilant.
Alkene: An unsaturated hydrocarbon containing at least one carbon–carbon double bond. Alkenes are common starting materials for epoxide synthesis by epoxidation.
Tetrahydrofuran: A five-membered saturated cyclic ether with the formula C4H8O. This common cyclic ether is less strained and typically less reactive than an epoxide.
Regioselectivity: The preference of a reaction for forming one constitutional isomer over other possible isomers. Epoxide opening can occur at either carbon, and conditions influence which position reacts.
Epichlorohydrin: A chlorinated epoxide used chiefly to manufacture epoxy resins and other chemicals. Its epoxide and chlorine groups make it a useful precursor to resin components.

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