"Epoxides (oxiranes) are widely used as versatile synthetic intermediates because regio- and stereoselective methods exist both for their construction and subsequent reactions. Reactions of epoxides are dominated by the electrophilic nature of the strained three-membered ring, which is susceptible to attack by a variety of nucleophiles. … The reaction of alkenes with peroxy acids provides for convenient and selective oxidation of double bonds. … Epoxidation involves an electrophilic syn-addition of the oxygen moiety of the peroxy acid to the double bond. The concerted formation of two new C-O bonds ensures that the reaction is stereospecific: cis-alkenes furnish the corresponding cis-epoxides and trans-alkenes the corresponding trans-isomers (racemic)."
Quote Details
Added by wikiquote-import-bot
Unverified quote
0 likes
Original Language: English
Available Languages (1)
Sources
Revision History
No revisions have been submitted for this quote.
Categories
Epoxide
8 quotes on TrueQuotesView all quotes by Epoxide →
Related Quotes
"Oxidation of α,β-unsaturated ketones with alkaline hydrogen peroxide produces the corresponding keto epoxides in good…"
"Dirnethyldioxirane (DMDO) is a mild reagent for epoxidation under neutral conditions of electron-rich as well as of e…"
"The reaction of chloro- or bromohydrins with bases provides an economical route for the preparation of epoxides. Halo…"
"Chloroiodomethane on treatment with methyllithium-lithium bromide or n-butyllithium at low temperature undergoes lith…"
"The inherent strain (-27 kcal/mol) of epoxides makes them prone to (1) ring opening by a wide range of nucleophiles, …"
"Although epoxidation of cyclic alkenes occurs preferentially from the less hindered side, the presence of a polar sub…"
"Straight-chain allylic alcohols have been crucial to the development of stereoselective syntheses of complex natural …"
"Many oxidants transform acyloins (α-hydroxy ketones) into α-diketones. Copper and bismuth oxidants are commonly selec…"
"The question of how one chooses appropriate carbon-carbon bond disconnections is related to functional group manipula…"
"The structural features that make it possible to classify compounds into families are called functional groups. ... T…"