Oxidations styrene oxide

Sikov MR, Cannon WC, Carr DB. 1980. Teratologic assessment of butylene oxide, styrene oxide and methyl bromide. Report to National Institute for Occupational Safety and Health, Division of Biomedical and Behavioral Science, U.S. Department of Health, Education and Welfare, Cincinnati, OH, by Battelle, Pacific Northwest Laboratory, Richland, WA. NTIS No. PB81-168510. 

Sikov MR, Cannon WC, Carr DB Teratologic Assessment of Butylene Oxide, Styrene Oxide and Methyl Bromide. DHHS (NIOSH) Pub No 81-124. US Department of Health and Human Services, July 1981... 

Sikov, M.R., Cannon, W.C., Carr, D.B., Miller, R.A., Montgomery, L.F. Phelps, D.W. (1981) Teratologic Assessment of Butylene Oxide, Styrene Oxide and Methyl Bromide, Cincinnati, OH, United States Department of Health and Hrunan Services, Public Health Service, Centers for Disease Control, National Instute for Occupational Safety and Health... 

Several 2-thienylaodiums have likewise been treated, with epoxides to obtain the corresponding 2-( -hydroryalkyl)thiophene (Eq. 801. Among the epoxides examined in this connexion are ethylene oxide, propylene oxide, styrene oxide, 1, 2-epoxy-3-butene, and. epichloro-hydrin ... 

Anderaaon 0 has determined pseudo finat-order rate constants for the reaction of exoees ammonia with a variety of epoxides, ranging from ethylene oxide itself to tefcramethylethylen oxide, and including also oyolohexene oxide, styrene oxide, and glyoidol. The least reactive substance studied, tetramethylethylenc oxide, was found to react 600 times more slowly than ethylene oxide. Curiously enough, on the other hand, glyoidol, styrene oxide, and ethylene oxide all roar ted at comparable rates. 

Halogenated methanes Propylene oxides Styrene oxides Nitrofurans... 

Ammonia and amines open oxide rings to form amino alcoholthe yields are markedly higher when amines are employed (55-90% vs. 18-40%).The ready availability of ethylene and propylene oxides makes this procedure attractive for preparing 2 dialkylaminoethanols and l-dialkylamino-2-propanols. Thus /3-diethylaminoethanol is conveniently prepared by the addition of ethylene oxide to diethylamine in methanol at 45° to 60° or by a combination of the two reactants in an autoclave at 100° (81%). Isopropylamine reacts with ethylene oxide in the presence of water and a small amount of hydrochloric acid to form /3-isopropylaminoethanol (76%). The reaction is general and is shown by higher oxides like isobutylene oxide/ styrene oxide/ and stilbene oxide/ ... 

BaHe has also been employed to study the behavior of styrene oxide, o- and p-methylstyrene oxides, 1-phenylpropene oxide isomers, and 2-methyl-l-phenylpropene oxide. Styrene oxide yields mainly the primary alcohol. Phenyldimethyloxirane is transformed in accordance with Eq. 170. ... 

Jones and Savill ( 6) have described the very rapid catalytic effect upon trimerization of isocyanates by ethylene oxide, propylene oxide, styrene oxide, or epichlorhydrin when a trace of pyridine is present. No reaction occurs in the absence of pyridine. They express the opinion that the function of the tertiary base is to open the epoxide ring and that the catalytic action is believed due to initial formation of... 

Styrene-7,8-oxide (styrene oxide), the major metabolite of the commercially important chemical styrene, was used as a model electrophile. Styrene is widely used in the manufacture of reinforced plastics and occupational exposure occurs mainly through inhalation of the vapor (14.). The metabolite styrene oxide is mutagenic in both prokaryotic (12) and eukaryotic test systems (16.171 and carcinogenic in rodents (18.). The formation of covalent DNA adducts with styrene oxide in vitro has been reported (18), therefore the development of procedures with the potential for the identification and assessment of styrene oxide damage in vivo clearly need to be explored. 

Key Words Ethylene oxide, Propylene oxide. Epoxybutene, Market, Isoamylene oxide. Cyclohexene oxide. Styrene oxide, Norbornene oxide. Epichlorohydrin, Epoxy resins, Carbamazepine, Terpenes, Limonene, a-Pinene, Fatty acid epoxides, Allyl epoxides, Sharpless epoxidation. Turnover frequency, Space time yield. Hydrogen peroxide, Polyoxometallates, Phase-transfer reagents, Methyltrioxorhenium (MTO), Fluorinated acetone, Alkylmetaborate esters. Alumina, Iminium salts, Porphyrins, Jacobsen-Katsuki oxidation, Salen, Peroxoacetic acid, P450 BM-3, Escherichia coli, lodosylbenzene, Oxometallacycle, DFT, Lewis acid mechanism, Metalladioxolane, Mimoun complex, Sheldon complex, Michaelis-Menten, Schiff bases. Redox mechanism. Oxygen-rebound mechanism, Spiro structure. 2008 Elsevier B.V. 

The 1H- and 13C-NMR spectra of the products obtained from propylene oxide, styrene oxide, and cyclohexene oxide show two CH3S-signals. 

YAN Yang, Z., Crothers, M., Attwood, D., Collett, J.H., Ricardo, N.M.P., Martini, L.G.A., and Booth, C., Association properties of ethylene oxide/styrene oxide diblock copolymer E17S8 in aqueous solution, J. Colloid Interface Sci., 263, 312, 2003. 

The reactivity order of epoxides is in accordance with their steric requirements. 1,2-Butylene oxide, styrene oxide, cyclohexene oxide, and l-methyl-1,2-cyclohexene oxide consume 1 equiv of hydride within 0.25, 1.0, 1.5, and 24 h, respectively. The ring opening of the epoxide occurs from the less hindered side and affords the Markovnikov alcohol, in quantitative yield (Chart 25.10) [18]. 

The hydroformylation of ethylene oxide gives acrolein in very low yields, which is not surprising in view of its extraordinary reactivity in the main, resinous products are obtained. The reactions of ethylene oxide, propylene oxide, cyclohexene oxide, styrene oxide and epichlorhydrin were studied by Takegami et al. [297] at normal conditions. They found that generally internal and conjugated olefin oxides were more reactive than terminal ones and established the following order of reactivity cyclohexene oxide (appr. 5) > styrene oxide > propylene oxide (1) > ethylene oxide epichlorhydrin (1/20-1/10) (the numbers give the relative reactivity). 

Although in photocurable formulations, difunctional oxirane derivatives are employed for mechanistic studies, monofunctional oxiranes are used including cyclohexene oxide, styrene oxide, or phenyl glycidyl ether. These studies indicate that the cationic polymerizations proceeding as a result of photoinitiation by onium salts have typical characteristics of polymerizations initiated by strong protonic adds. Thus, initiation involves protonation of oxirane ring while propagation proceeds on tertiary oxonium ions as active species, that is, by the ACE mechanism. 

Toxicity of the polyamines can, however, be avoided by using modified aliphatic polyamines. These are obtained by the addition of polyamines to a variety of compounds such as diglycidyl ether, ethylene oxide, styrene oxide, halohydrin ethers and acrylonitrile or with polymers containing functional groups known to react with amines (other than epoxides). 

---