Phenylethylene oxide

Synonyms Epoxyethylbenzene epoxystyrene phenylethylene oxide phenyloxirane styrene-7,8-oxide... 

Phenylethylene oxide might be expected among the oxidation products from ethylbenzene by similar reactions. Its absence may be caused by the relative reluctance of styrene to react with peroxy radicals. a-Methylstyrene, which can yield the more stable -substituted a-methyl-a-phenethyl radical, is 2 to 3 times as reactive towards peroxy radicals as is styrene (22). 

An instanee in which the solvent appears to affect not merely the stereochemistry but also the direction of ring cleavage had been described previously by Jorlfcnder.8 Treatment of l-(p anisyl-)-2-phenylethylene oxide of unspecified configuration with hydrogen... 

SYNS EPOXYETHYLBENZENE (SCI) EPOXYSTYRENE 0,P-EPOXYSTYRENE NCI-C54977 PHENETHYLENE OXIDE l-PHENYL-1,2-EPOXYETHANE PHENYLETHYLENE OXIDE PHENYLOXIRANE 1-PHENYLOXIRANE 2-PHENYLOXIRANE STYRENE EPOXIDE STYRENE OXIDE STYRENE-7,8-OXIDE STYRYL OXIDE... 

PHENYLETHYLENE see SMQOOO PHENYLETHYLENE OXIDE see EBROOO 2-PHENYL-2-ETHYLGLUTARIC ACID IMIDE see DYC800... 

PHENYLETHYLENE OXIDE (96-09-3) Combustible liquid (flash point 165°F/74°C). Violent reaction with strong oxidizers, nitric acid, sulfuric acid. Reacts with acids, alkalis, and some salts, possibly causing explosive polymerization. See also Styrene. 

Beilstein Handbook Reference) AI3-18151 Benzene, (1,2-epoxyethyl)- Benzene, (epoxy-ethyl)- BRN 0108582 CCRIS 1268 EINECS 202-476-7 EP-182 Epoxyethyl benzene Epoxystyrene Fenyloxiran HSDB 2646 NCI-C54977 NSC 637 Oxirane, phenyl- Phenethylene oxide Phenyl oxirane Phenylethylene oxide Phenyloxitane Styrene-7,8-oxide Styrene epoxide Styrene oxide Styryl oxide. Liquid mp = -35.6 bp b 194.1 d B 1.0523 Xm = 261 nm (cyclohexane) insoluble in H2O, soluble in EtOH, Et20, CHCI3. 

Rabe s (56) and Schmidt s (24) experiments, that is, decomposition of the trimethylammonium hydroxides of ephedrine and -ephedrine, to stereoisomeric l-methyl-2-phenylethylene oxides, lead to the same inference. This hydramine degradation occurs in compounds with vicinal hydroxyl and amino groups, and is indicated by the reaction scheme on p. 362. 

Alternative Names/Abbreviations Epoxyethylbenzene, epoxystyrene, phenylethylene oxide, phenyloxirane... 

CAS 96-09-3 EINECS/ELINCS 202-476-7 Synonyms Benzene, (epoxyethyl) Epoxyethylbenzene 1,2-Epoxyethylbenzene 1,2-Epoxy-1-phenylethane Epoxystyrene a,p-Epoxystyrene Oxirane, phenyl- Phenethylene oxide 1-Phenyl-1,2-epoxyethane Phenylethylene oxide Phenyloxirane 1-Phenyloxirane 2-Phenyloxirane Styrene epoxide Styrene-7,8-oxide... 

In a 250 ml. distilling flask (1) place 122 g. (119 ml.) of p-phenylethyl alcohol and 40 g. of sodium hydroxide peUets (or 56 g. of potassium hydroxide). Heat is evolved. Warm gently until bubbles commence to form and the mixture separates into two sharply-defined layers. Distil slowly water, etc. passes over first accompamed by the gradual dis appearance of the upper phase. FinaUy the styrene passes over at 140 160° (mainly 150°) coUect this separately in a receiver containing about 0 1 g. of hydroquinone. Dry the distillate with a httle anhydrous calcium chloride or magnesium sulphate, and then distil under reduced pressure (2). C oUect the pure styrene at 42-43°/18 mm. The 3rield is 80 g. Add about 0-2 g. of hydroquinone (anti-oxidant) if it is desired to keep the phenylethylene. 

Hydroxy(tosyloxy)iodobenzene 2014 reacts with phenyltrimethylsilane 81 in boiling acetonitrile to give diphenyliodonium tosylate 2015 and trimethylsilanol 4 or HMDSO 7 [184, 185]. Likewise, treatment of 2,5-bis(trimethylsilyl)furan 2016 with 2014 in boiling acetonitrile/methanol affords 78% iodonium tosylate 2017 and trimethylsilanol 4 [185]. In the presence of Bp3-OEt2 iodosobenzene oxidizes allyl-trimethylsilanes such as 2018 to unsaturated aldehydes such as 2019 in 63% yield, with formation of iodobenzene and trimethylsilanol 4 [186]. Analogously, vinyltrimethylsilanes such as (Z)-l-trimethylsilyl-2-phenylethylene 2020 afford, via 2021, acetylenes such as phenylacetylene in 61% yield and iodobenzene and trimethylsilanol 4 [187] (Scheme 12.54). 

Several groups have described syntheses of chromones which involve the use of enamines. Reaction of salicylaldehyde with 1-morpholinocyclohexene gives the chromanol which is readily oxidized to the chromone (66JOC1232). Other examples include the use of 1-morpholino-l-phenylethylene which gives flavene, whilst N-styrylmorpholine yields isoflavone. The enamine reaction is considered to proceed in the normal manner with subsequent cyclization involving the neighbouring phenolic group (Scheme 163). 

Styrene is phenylethylene, c-C6Hu-CH=CH2, a compound important in a number of polymerizations. In the body, the cytochrome P450 enzyme in the liver can form styrene oxide, which then may react with the organisms DNA, i.e become a carcinogen. The use of MB in lipid fdms to oxidize styrene has been achieved by Rusling et al. (1997) in a series of reactions that can be written as follows ... 

Coupling, of benzenediazonium chloride with acetoacetic acid, 32, 84 of diazotized />-aminoacetophenone with quinone, 34, 1 of diazotized 3,5-dichloro-2-aminoben-zoic acid to give 4,4, 6,6 -tetra-chlorodiphenic acid, 31, 96 of diphenyldichloromethane to tetra-phenylethylene, 31,104 Creased flask, 37, 55 Creosol, 33,17 Crotonaldehyde, 33, 15 34, 29 diethyl acetal, 32, 5 Cupric acetate monohydrate, 36, 77 Cuprous oxide-silver oxide, 36, 36, 37 Cyanamide, 34, 67 36, 8 Cyanoacetamide, 32, 34 Cyanoacetic acid, 31, 25 38, 16, 18 Cyanoacetylurca, 37,16 /i-Cyanobenz d[Pg.99]

Photochemical reactions of substituted phenylethylenes, frans-stilbene and 1,1-diphenylethylene, on silica gel, has been reported by Sigman et al. [40]. Irradiation of fraus-slilbcnc adsorbed on silica gel produced two dimers, along with ds-stilbene, phenanthrene, and a small amount of ben-zaldehyde which arose from a type II oxidation mechanism (Scheme 9). The formation of photodimers was claimed to be promoted by inhomogeneous surface loading and slow diffusion of fraus-slilbcnc on silica [40]. 

Oxygenation of C=C and—C=C—. 9,10-Dicyanoanthracene (DCA) sensitizes photooxygenation of some alkenes in CH,CN. The reaction does not involve singlet oxygen and is believed to involve electron transfer. Thus tetra-phenylethylene is oxidized in this way mainly to benzophenone (equation I). Under the same conditions trans-stilbene is oxidized to benzaldehyde. Sulfides are oxidized to sulfoxides and/or sulfones. ... 

Staudinger and Pfenninger long ago suggested that addition of sulfur dioxide to diphenylketene gives an intermediate, 3,3-diphenyl-l,2-oxathietane-4-one 2-oxide, that decomposes to diphenylsulfene and carbon dioxide, the former yielding tetra-phenylethylene. Similar intermediates were proposed for the addition of sulfur dioxide to pentamethyleneketene, ketenimines, " ethylene, 1,1-difluoro-ethylenes, and an aluminum trichloride derivative of the 1,2,3,4-tetramethyl-cyclobutene cation. An intermediate adduct 494 actually has been isolated at... 

PHENYLETHYLENE (100-42-5) CgHg Forms explosive mixture with air [explosion limits in air (vol %) 1.1 to 6.1 flash point 88°F/31°C autoignition temp 914°F/490°C Fire Rating 3]. Unless inhibited (often with teri-butylcatechol however, it should be noted that the presence of an inhibitor may only lessen the possibility of polymerization), polymerization may occur and container may explode. Polymerization can be caused by elevated temperatures above 151°F/66°C contact with azoisobutyronitrile, butyl lithium, oxidizers, peroxides and hydroperoxides (dibenzoyl... 

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