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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.
It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening.
Diepoxybutane (also known as butane diepoxide, butadiene diepoxide, or 1,2:3,4-diepoxybutane) is an epoxide which is a colorless liquid at room temperature. Epoxides are very reactive due to ring strain and diepoxybutane contains two of these groups, so it is highly reactive, more than other ethers.
Other processes may take place competitively under basic conditions, particularly when β-elimination is slow or not possible. [6] These pathways likely begin with lithiation of a carbon in the epoxide ring, followed by α-elimination to afford a carbene intermediate. 1,2-hydrogen migration leads to ketones, [2] while intramolecular C–H insertion affords cyclic alcohols with the formation of ...
The mechanism of homogeneous ring-opening metathesis polymerization is well-studied. It is similar to any olefin metathesis reaction. Initiation occurs by forming an open coordination site on the catalyst. Propagation happens via a metallacycle intermediate formed after a 2+2 cycloaddition. When using a G3 catalyst, 2+2 cycloaddition is the ...
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Since unsymmetrical epoxides are chiral, the bis epoxide consists of three stereoisomers, although these are not separated. Bisphenol A diglycidyl ether slowly hydrolyzes to 2,2-bis[4(2,3-dihydroxypropoxy)phenyl)propane (bis-HPPP). Similarly, DGEBA reacts with acrylic acid to give vinyl ester resins. The reaction results in opening of the ...