α,β‐Unsaturated carbonyl compounds can be prepared by the oxidation of trimethylsilyl enol ethers with IBX (1) or IBX⋅MPO (2).A diverse set of carbonyl compounds can be dehydrogenated with ease by using this method. Rubottom Oxidation. Yields have been strongly influenced … Here we describe rearrangements of those compounds, triggered by epoxidation of their enol ethers that completely remodel their structures, essentially turning them “inside out”. Epoxidation Alcoholysis of Cyclic Enol Ethers Catalyzed by Ti (OiPr) 4 or Venturello′ s Peroxophosphotungstate Complex. Asymmetric epoxidation of enol ethers and esters using iminium salt catalysts synthesis of α-Hydroxy-Carbonyls Tools RDF+XML BibTeX RDF+N-Triples JSON RefWorks Dublin Core Simple Metadata Refer METS HTML Citation ASCII Citation OpenURL ContextObject EndNote OpenURL ContextObject in Span MODS MPEG-21 DIDL EP3 XML Reference Manager RDF+N3 Multiline CSV Recent Literature. … Doctor of Philosophy .

An epoxide is a cyclic ether with a three-atom ring.
identify the product formed from the reaction of a given epoxide with given base.
Asymmetric Epoxidation of Enol Ethers and Esters Using Iminium Salt Catalysts Synthesis of α-Hydroxy-Carbonyls . By Saud Muslih Almutairi . A thesis submitted is partial fulfilment of the requirements for the degree of . anita.orendt@utah.edu

write an equation to illustrate the cleavage of an epoxide ring by a base. reaction of alkynyl hemiketals that delivered polycyclic, enol-ether-containing spiroketals. explain why epoxides are susceptible to cleavage by bases, whereas other cyclic ethers are not. The Role of Asynchronous Bond Formation in the Diastereoselective Epoxidation of Cyclic Enol Ethers: A Density Functional Theory Study Anita M. Orendt,*,‡ Scott W. Roberts,† and Jon D. Rainier*,† Department of Chemistry, 315 South 1400 East, UniVersity of Utah, Salt Lake City, Utah 84112-0850, and Since enol ethers and esters are types of olefin, some asymmetric epoxidation and dihydroxylation reactions have been applied to their oxidation. United Kingdom . [1] Due to the high level of substitution on the carbon skeletons of Orendt AM(1), Roberts SW, Rainier JD. University of East Anglia . United Kingdom . Epoxidation–alcoholysis of cyclic enol ethers catalyzed by Ti(O i Pr) 4 or Venturello's peroxophosphotungstate complex Pieter Levecque , ab David Gammon , b Henok Hadgu Kinfe , † b Pierre Jacobs , a Dirk De Vos a and Bert Sels * a University of East Anglia . This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers.They are produced on a large scale for many applications. Various ionic liquids have been tested for the preparation of silyl enol ethers from aldehydes and ketones with (bistrimethylsilyl)acetamide (BSA). Oxidative C−O coupling of silyl enol ethers leads to the formation of α‐acyloxyketones with a free carboxylic acid group. The enol ether double bond is epoxidized by the peracid. The oxidation of enol ethers and their derivatives is a useful method for the synthesis of α-hydroxy- ketones or their derivatives, which are versatile building blocks for organic synthesis. We recently discovered a tandem cycloisomerization–dimerization reaction of alkynyl hemiketals that delivered polycyclic, enol‐ether‐containing spiroketals. The synthesis of α-hydroxy ketones is achieved by reaction of silyl enol ethers with mCPBA, with subsequent rearrangement. A specially developed preparative one‐pot procedure transforms ketones via silyl enol ethers formation and the following coupling into α‐acyloxyketones with yields 35–88%.


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