F Allyl ethyl ether

Individually indexed compounds include f Allyl ethyl ether, 1955... 

Peroxides. These are formed by aerial oxidation or by autoxidation of a wide range of organic compounds, including ethyl ether, allyl ethyl ether, allyl phenyl ether, benzyl ether, benzyl butyl ether, n-butyl ether, /50-butyl ether, f-butyl ether, dioxane, tetrahydrofuran, olefines, and aromatic and saturated aliphatic hydrocarbons. They accumulate during distillation and can detonate violently on evaporation or distillation when their concentration becomes high. If peroxides are likely to be present materials should be tested for peroxides before distillation (for tests see entry under "Ethers", in Chapter 2). Also, distillation should be discontinued when at least one quarter of the residue is left in the distilling flask. 

ALLYL ETHYL ETHER (557-31-3) Forms explosive mixture with air (flash point <70°F/21 °C). May form explosive peroxides during storage. Flow or agitation of substance may generate electrostatic charges due to low conductivity. Violent reaction with strong oxidizers, strong acids. 

ALLYL PHENYL ETHER (1746-13-0) C ipO Combustible liquid (flash point 143°F/62°C). May form peroxides on contact with air. Violent reaction may occur with strong oxidizers, strong acids acetyl peroxide boron trifluoride aluminum hydride (possible explosion). Incompatible with nitrosyl perchlorate, ozone (may form explosive ethyl peroxide, aldehyde and acetic acid). On small fires, use dry chemical powder (such as Purple-K-Powder), foam, or CO2 extinguishers. 

A. J. Colussi, F. Zabel, and S. W. Benson, The very low-pressure pyrolysis of phenyl ethyl ether, phenyl allyl ether, and benzyl methyl ether and the enthalpy of formation of the phenoxy radical, Int. J. Chem. Kinet. IX 161-178 (1977). 

Ac, acetyl AIBN, azobis(isobutanonitrile) All, allyl AR, aryl Bn, benzyl f-BOC, ferf-butoxycarbonyl Bu, Butyl Bz, benzoyl CAN, ceric ammonium nitrate Cbz, benzyloxycarbonyl m-CPBA, m-chloroperoxybenzoic acid DAST, diethylaminosulfur trifluoride DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, /V. /V - d i eye I oh e x y I c ar bo -diimide DCM, dichloromethyl DCMME, dichloromethyl methyl ether DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DEAD, diethyl azodicarboxylate l-(+)-DET, L-(+)-diethyl tartrate l-DIPT, L-diisopropyl tartrate d-DIPT, D-diisopropyl tartrate DMAP, 4-dimethylaminopyridine DME, 1,2-dimethoxyethane DMF, /V./V-dimethylformamide DMP, 2,2-dimethoxypropane Et, ethyl Im, imidazole KHMDS, potassium hexamethyldisilazane Me, methyl Me2SO, dimethyl sulfoxide MOM, methoxymethyl MOMC1, methoxymethyl chloride Ms, methylsulfonyl MS, molecular sieves NBS, N-bromosuccinimide NIS, /V-iodosuccinimide NMO, /V-methylmorpho-line N-oxide PCC, pyridinium chlorochromate Ph, phenyl PMB, / -methoxvbenzyl PPTs, pyridiniump-toluenesulfonate i-Pr, isopropyl Py, pyridine rt, room temperature TBAF, tetrabutylammonium fluoride TBS, ferf-butyl dimethylsilyl TBDMSC1, f-butylchlorodimethylsilane Tf, trifhioromethylsulfonyl Tf20, trifluoromethylsulfonic anhydride TFA, trifluoroacetic acid THF, tetrahydrofuran TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate / -TsOH. / -toluenesulfonic acid... 

A solution of ethyl nitroacetate (1.06 mmol, 2.5 equiv), DABCO (0.10 equiv), and allyl alcohol (0.424 mmol, 1 equiv) in ethanol (1.4 ml) was stirred for 36 h in a sealed vessel (Schlenk) at 80 °C. The solvent was then removed and the residue purified by chromatography hexane/diethyl ether 6 1 then diethyl ether, / f = 0.31. Ethyl 5-(hydroxymethyl)-4,5-dihydro-3-isoxazolecarboxylate 70 mg, 95%. 

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