Phenyloxirane Styrene Oxide

The formation of cyclic dimer (2-10 % yield) in the cationic polymerization of styrene oxide was reported by different authors 25 27). More recently, Yamashita studied the catonic oligomerization of styrene oxide in the presence of various Lewis and protic acids as initiators (SnCl4, BF3 0(C2H5)2, HOS02CF,) and found a 100 o conversion to cyclic oligomers with n = 2-5 28). 

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This enantioselective reduction can be used for synthesis of chiral 1-substituted oxiranes.1 2 3 Thus reduction of 2-chloroacetophenone with B2H6 catalyzed by 1 (1 mole %) results in (S)-( + )-(chloromethyl)benzenemethanol, which in the presence of base converts to (S)-( - )-phenyloxirane (styrene oxide). 

Cognate preparations. Phenyloxirane (styrene oxide). Use of perbenzoic acid. Use 42 g (0.29 mol) of perbenzoic acid (CAUTION, see Section 4.2.56, p. 455), in 350 ml of dichloromethane and 30 g (0.29) of styrene in 100 ml of dichloromethane. Stir the reaction mixture at 0 °C for 24 hours. Only a slight excess of peracid remains confirm this by mixing an aliquot portion with excess of acidified potassium iodide and titrating with standard sodium thiosulphate solution. Work-up as described above and distil the dried dichloromethane solution through an efficient fractionating column. Styrene oxide passes over at 189-192 °C (or at 101 °C/40mmHg) the yield is 25 g (72%). 

Nucleophilic ring opening of epoxides usually occurs with anti stereochemistry, with nucleophilic attack at the less substituted carbon. On the other hand, the acid-catalyzed epoxidation-hydrolysis sequence is not always stereospecific. In the case of (5 )-l-phenyloxirane (styrene oxide), the acid-catalyzed ring opening is regiose-lective and proceeds through the more stable (benzylic) carbocation there is extensive racemization because of the involvement of a carbocation. ... 

Cristol, Douglass, and Meek211 treated 2-phenyloxirane (styrene oxide) with phenyllithium and obtained -phenylphenethyl alcohol (1,2-diphenyl-ethanol) ... 

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

Ethylenic compounds when oxidised with perbenzoic acid or perphthalic acid in chloroform solution yield epoxides (or oxiranes). This is sometimes known as the Prileschajew epoxidation reaction. Thus styrene affords styrene oxide (or 2-phenyloxirane) ... 

Epoxy ethylbenzene, Styrene oxide, see Phenyloxirane, 2949b... 

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... 

The preparation of styrene oxide (phenyloxirane) may be described as an example 33 Styrene (30 g, 0.29 mole) is added to a solution of peroxybenzoic acid (42 g, 0.30 mole) in chloroform (500 ml), and the mixture is set aside at 0° for 24 h, being repeatedly shaken during the first few hours. Completion of the oxidation can be determined by titration of an aliquot part of the chloroform solution. Then the benzoic acid formed and the small excess of peroxybenzoic acid are removed by repeated extraction with 10% sodium hydroxide solution, and the organic phase is washed with water until free from alkali and then dried over sodium sulfate. Fractional distillation affords styrene oxide (24-26 g, 70-75 %) as a colorless liquid, b.p. 101°/40mm. 

Phenylnitrobenzene. See 2-Nitro-1,1 -biphenyl Phenyl 2-nitrophenylamine. See 2-Nitrodiphenylamine N-Phenyl-p-nitrosoaniline. See p-Nitrosodiphenylamine Phenyloxirane 1-Phenyloxirane 2-Phenyloxirane. See Styrene oxide Phenyl paraben... 

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... 

Styrene oxide (2-phenyloxirane) is polymerized by cations produced under irradiation, as shown in Equation (1.108) ... 

Styrene oxide see Phenyloxirane ... 

Predict the product of the reaction of styrene oxide (phenyloxirane) in an acid-catalyzed reaction with methanol. 

The oxidation of styrene in a dichloroethane/aq. H2O2 system, in the presence of RuCla and Me2N (dodecyl)2 Br at 80 °C affords benzaldehyde (64 %), benzoic acid (6 %), and phenyloxirane (4 %). The quaternary ammonium salt extracts both H2O2 and RUCI3 into the organic phase [60]. 

PHENYLOXIRANE or 1-PHENYLOXIRANE (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. 

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