Oxirane phenyl

Styrene oxide Benzene, (epoxyethyl)- (8) Oxirane, phenyl- (9) (96-09-3)... 

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. 

Oxirane, phenyl-. See Styrene oxide Oxirane, (trichloromethyl)-. See 1,2-Epoxy-3,3,3-trichloropropane Oxirane, trifluoro (trifluoromethyl)-. See 1,2-Epoxy-1,1,2,3,3,3-hexafluoropropane Oxirene, 2,2,2-trichloroethyl-. See Trichlorobutylene oxide Oxitol. See Ethoxyethanol Oxoacetic acid. See Glyoxalic acid 5-Oxobarbituric acid monohydrate. See Alloxan monohydrate... 

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... 

Organoboranes are reactive compounds for cross-coupling[277]. The synthesis of humulene (83) by the intramolecular cross-coupling of allylic bromide with alkenylborane is an example[278]. The reaction of vinyiborane with vinyl-oxirane (425) affords the homoallylic alcohol 426 by 1,2-addition as main products and the allylic alcohol 427 by 1,4-addition as a minor product[279]. Two phenyl groups in sodium tetraphenylborate (428) are used for the coupling with allylic acetate[280] or allyl chloride[33,28l]. 

Durst and coworkers were the first to report the condensation of chiral a-sulphinyl carbanions with carbonyl compounds477. They found that metallation of ( + )-(S)-benzyl methyl sulphoxide 397 followed by quenching with acetone gives a mixture of dia-stereoisomeric /i-hydroxy sulphoxides 398 in a 15 1 ratio (equation 233). The synthesis of optically active oxiranes was based on this reaction (equation 234). In this context, it is interesting to point out that condensation of benzyl phenyl sulphoxide with benzaldehyde gave a mixture of four / -sulphinyl alcohols (40% overall yield), the ratio of which after immediate work-up was 41 19 8 32478. 

Mit Natriumboranat gelingt es z. B. 3-Brommethyl-2-phenyl-oxiran (HMPT/700, 12 Stdn.) zum 3-Methyl-2-phenyl-oxiran (63% d.Th.) zu reduzieren1. 

Tab. 33 Alkohole durch Reduktion von Phenyl-oxiran mit verschiedenen Hydriden...

Um einen prim. Alkohol zu erhalten, muG also das a-Kohlenstoff-Atom des aliphati-schen Epoxids tertiar sein8. Bei aromatisch substituierten Oxiranen (z.B. Phenyl-oxiran) geniigt ein Substituent. Als Beispiele dienen die Reduktionen von 2-Athyl-2-(4-chlor-phenyl)-oxiran mit Lithiumalanat oder Aluminiumhydrid9 ... 

Vvahrend Phenyl-oxiran hauptsachlich invers geoffnet wird, reagieren Monoalkyl-oxirane ahnlich wie mit ge-mischtcn Aluminiumhydriden hauptsachlich nach Markownikow6. 

Analog ergibt 2-Methyl-2-phenyl-oxiran 2-Phenyl-propanol (100% d. Th.) und tram-3-Methyl-2-phenyl-oxiran l-Phenyl-propanol-(2) (97% d.Th.). 

Propylene oxide Butylene oxide Phenyl oxirane ... 

Reaction of the carbanion of chloromethyl phenyl sulphoxide 409 with carbonyl compounds yields the corresponding 0-hydroxy adducts 410 in 68-79% yield. Each of these compounds appears to be a single isomer (equation 242). Treatment of adducts 410 with dilute potassium hydroxide in methanol at room temperature gives the epoxy sulphoxides 411 (equation 243). The ease of this intramolecular displacement of chloride ion contrasts with a great difficulty in displacing chloride ion from chloromethyl phenyl sulphoxide by external nucleophiles . When chloromethyl methyl sulphoxide 412 is reacted with unsymmetrical ketones in the presence of potassium tcrt-butoxide in tert-butanol oxiranes are directly formed as a mixture of diastereoisomers (equation 244). a-Sulphinyl epoxides 413 rearrange to a-sulphinyl aldehydes 414 or ketones, which can be transformed by elimination of sulphenic acid into a, 8-unsaturated aldehydes or ketones (equation 245). The lithium salts (410a) of a-chloro-/ -hydroxyalkyl... 

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