Epoxy allylic ether

Epoxides can also be converted to 1,3-dioxolanes by treatment with acetone in the presence of catalytic amounts of bismuth(lll) salts, with yields ranging from 87-99%. For example, the epoxy allyl ether 98 provided the dioxolane 99 in 97% yield using bismuth triflate as the catalyst <01SC3411>. When simple epoxides are treated with Aw(triphenylphosphine)-iminium cobalt tetracarbonyl (PPN-Co(CO)4) under Lewis acid catalysis, a carbonyl insertion reaction provides p-lactones regioselectively in good to high yields. The carbonylation occurs selectively at the unsubstituted position, and the reaction is... 

Synonyms AGE AI3-37791 AllyE2,3-epoxypropyl ether l-Allyloxy-2,3-epoxypropane BRN 0105871 CCRIS 2375 EINECS 203-442-4 l,2-Epoxy-3-allyloxypropane Glycidyl allyl ether M 560 NC1-C56666 NSC 18596 [(2-Propenyloxy)methyl]oxirane UN 2219. 

Unsaturated fatty acid Acrylates Isocyanate Allyl ether Maleaie Epoxy... 

Allyl chloride is used to make intermediates for downstream derivatives such as resins and polymers. Approximately 90% of allyl chloride production is used to synthesize epichlorohydrin, which is used as a basic building block for epoxy resins and in glycerol synthesis. Allyl chloride is also a starting material for allyl ethers of phenols, bisphenol A and phenolic resins, and for some allyl esters. Other compounds made from allyl chloride are quaternary amines used in chelating agents and quaternary ammonium salts, which are used in water clarification and sewage sludge flocculation (Kneupper Saathoff, 1993). 

Tetrabromobisphenol A (TBBPA) is primarily used as a reactive flame retardant in epoxy resin circuit boards. Both hydroxyl groups on TBBPA can be reacted with epichlorohydrin under basic conditions to form the diglycidyl ether, which is widely used in epoxy resin formulations. TBBPA is also used in polycarbonate and ether polyester resins and is used as a chemical intermediate for the synthesis of tetrabromobisphenol A allyl ether, -bis(2-hydroxyethyl ether), -carbonate oligomer, and -diglycidyl ether. TBBA is also used as a flame retardant in plastics, paper, and textiles, and as a plasticizer in adhesives and coatings. 

Epichlorohydrin or chloromethyloxirane is manufactured from allyl chloride, and, in 2006, had a merchant price of US 1.66 kg [4]. It is used as a building block in the manufacture of plastics, epoxy resins, phenoxy resins, and other polymers, and as a solvent for cellulose, resins, and paints, and has also found use as an insect fumigant. Epoxy resins (aryl glycidyl ethers) are manufactured successfully in large scale (1.2 x 10 metric tons in 2000) [26] and are widely used in a variety of industrial and commercial applications [27]. These are made by addition reactions of epichlorohydrins or by epoxidation of allyl ethers or esters (Table 1.1). Epichlorohydrin can be reacted with an alkali nitrate to produce glycidyl nitrate, an energetic binder used in explosive and propellant compositions. 

Curious about these strained products, we wondered if more rigid starting structure could be used for the Adler-Becker/Diels-Alder sequence (Scheme 10). We decided to see if chromanones could be substituted with benzofuian stractures. SUylation of resorcinol 44 was followed by bromination and cyclizatiOTi to form benzofuran 46. As shown previously, triahylatiOTi and allyl ether deprotection yielded ketone 47, which was subsequently reduced to the benzylic alcohol however, this required much harsher conditions than those in the chromanone series (LiAlHj vs. NaBHj). Although less efficient than the chromanone derivative, the Adler-Becker oxidation proceeded to provide epoxy benzofuranone 48... 

While allyl and glycidyl ethers are converted into a mixture of oxetane and oxepine products with xec-butyllithium, Mordini and co-workers reported that allyl, benzyl, and propargyl epoxy ethers can be regioselectively converted into 2-vinyl, 2-phenyl, or 2-aIkynyl-3-(hydroxyalkyl) oxetanes upon treatment with either Schlosser s base or other mixed metal bases. Some of the best results were obtained with the LDA/potassium ferf-butoxide mixture (LIDAKOR, ref 194). While rearrangement of propargylic or benzylic epoxide ethers formed exclusively the four-membered oxetanes, rearrangements of allyl oxiranyl ethers show a selectivity for cyclization to the seven-membered ring. Trialkylsilyl-substituted epoxide allyl ethers also show a preference for the oxepine, and mixtures are obtained as the size of the silyl substituents is increased (Scheme 17). 

Synonyms AGE Allyl-2,3-epoxypropyl ether 1-Allyloxy-2,3-epoxypro-pane 1,2-Epoxy-3-allyloxypropane Glycidyl allyl ether [(2-Propenyloxy) methyO oxirane Classification Glycidyl ether monomer Empirical CsHioOj Formula CH2CHCH20CH2=CH2CH0... 

Tetrabromobisphenol A di-2-hydroxyethyl ether Tetradecabromodiphenoxybenzene Tetrakis (2-chloroethyl) ethylene diphosphate Tris (2,3-dichloropropyl) phosphate flame retardant, EPS Tribromophenyl allyl ether flame retardant, ethyl cellulose Diphenyl octyl phosphate flame retardant, ethylene copolymers Ethylenebis (tetrabromophthalimide) flame retardant, expandable PS Dibromoethyidibromocyclohexane Tetrabromobisphenol A bis (allyl ether) Tetrabromocyclooctane flame retardant, extruded PS Tetrabromocyclooctane flame retardant, fabrics Antimony pentoxide Methylphosphonic acid, (5-ethyl-2-methyl-2-oxido-1,3,2-dioxaphosphorinan-5-yl) methyl methyl ester flame retardant, fibers Antimony pentoxide Tetrabromoethane flame retardant, filament winding Epoxy resin, brominated flame retardant, film Tetrabromobis (2-ethylhexyl) phthalate flame retardant, fire-retardant material Chlorinated paraffins (C12, 60% chlorine) Chlorinated paraffins (C23, 43% chlorine) flame retardant, flexible PU foam bedding Tetrakis (2-chloroethyl) ethylene diphosphate flame retardant, flexible PU foam furniture Tetrakis (2-chloroethyl) ethylene diphosphate flame retardant, flexible PU foam transportation Tetrakis (2-chloroethyl) ethylene diphosphate flame retardant, flexible PU foams furniture, automobile seating... 

A large variety of hyperbranched polymers with acrylate, vinyl ether, allyl ether, or epoxy functions were studied as multifunctional cross-linkers in coatings and in thermosets, using thermal as well as UV curing methods Clearly, polyesters are most prominent in the field, with the Perstorp Boltom products leading in technical studies. The commercialized poly(esteramide)s from DSM, sold under the trade name Hybrane polyethylenimines from BASF AG, available under the trade name TupasoF and poly(urethane)s (PUs) and polyesters developed by BASF are examples for hyperbranched polymers suited for coatings and resin products. 

The package stability of alcohol-soluble resole resins and their compatibility with epoxy resins can be improved by partial conversion of the methylol groups to ethers. Allyl ethers have been used with epoxy resins in interior can coatings. Low molecular weight butyl ethers are used with acid catalysts to cross-link epoxy resins and other hydroxy-substituted resins, by etherification and transetherification reactions (148). 

Racemic epoxy sulfone derivatives are easily prepared from allyl ethers by reaction with sodium/+toluenesulfinate in the presence of iodine followed by treatment with triethylamine, separation of E and Zisomers, and epoxidation with i BuOOH and /+BuLi in THF (eq 3). ... 

The primaiy use of TBBPA is as a flame letaidant in epoxy resin eireuit boards and in eleetrraiie enelosures made of poly-carbonate-aciylonitrile-butadiene-slyrene (PC-ABS). Other applieations of TBBPA inelude its use as a flame retardant for plastics, paper, and textiles as a plastieizer in adhesives and eoatings and as a ehemieal intermediate for the synthesis of other flame retardants (e.g., TBBPA allyl ether). It has also been applied to carpeting and office fiimiture as a flame retardant. 

HBP with acrylate, vinyl ether, allyl ether or epoxy functions were studied as multifunctional crosslinker [41-43] in coatings and thermosets [44,45]. 

Tanaka et al. 231) prepared (518a) from allylic alcohol (514) via the epoxy silyl ether (515), which was ring opened with diethylaluminum 2,2,6,6-tetramethylpiperidide to afford the 3-ene-l,2-diol (516) Scheme 90). 

A cascade reaction for the construction of spirobenzo[/t]chromanone and spiropyranone derivatives was achieved by a platinum-catalysed tandem cyclization/[l,2]-alkyl migra-tion/allyl shift of epoxy alkynyl allyl ethers followed an aromatic cyclization reaction (Scheme 142). ... 

Allyl Glycidyl Ether. This ether is used mainly as a raw material for silane coupling agents and epichlorohydrin mbber. Epichlorohydrin mbber is synthesized by polymerizing the epoxy group of epichlorohydrin, ethylene oxide, propylene oxide, and aHyl glycidyl ether, AGE, with an aluminum alkyl catalyst (36). This mbber has high cold-resistance. 

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