Phosphorylated epoxide

Lauth de Viguerie, N.. Willson. M.. and Perie, J., Synthesis and inhibition studies on glycolytic enzymes of phosphorylated epoxides and a-enones. New J. Chem., 18, 1183, 1994. 

The phosphorous-containing epoxides (80) are good, flame-resistant materials, especially when used for structural adhesives. A typical phosphorylated epoxide is based on bis-(3-glycidyloxyphenyl)methyl phosphine oxide (BGDDPMPO) ... 

The phosphorylated epoxide is low in smoke evolution high in char yield, and high in oxygen index. 

The pollutant (xenobiotic) forms a stable covalent bond with its target. Examples include the phosphorylation of cholinesterases by the oxon forms of OPs, the formation of DNA adducts by the reactive epoxides of benzo[a] pyrene and other PAHs, and the binding of organomercury compounds to... 

Other work has indicated that chlordane and heptachlor are energy transfer inhibitors as evidenced by marked decreases in oxidative phosphorylation of rat hepatic mitochondria following in vitro incubation of the mitochondria with the pesticides (Ogata et al. 1989). Interestingly, even though heptachlor epoxide is more toxic than either chlordane or heptachlor in tests of general toxicity, it was less effective in inhibiting mitochondrial respiration. 

Ergiiden, J.-K. Schaumann, E. Phosphoryl functionalized bishomoallyl alcohols by ring opening of epoxides with lithiated allyldiphe-nylphosphane oxide. Synthesis 1996, 707—710. 

Michael-aldol reaction as an alternative to the Morita-Baylis-Hillman reaction 14 recent results in conjugate addition of nitroalkanes to electron-poor alkenes 15 asymmetric cyclopropanation of chiral (l-phosphoryl)vinyl sulfoxides 16 synthetic methodology using tertiary phosphines as nucleophilic catalysts in combination with allenoates or 2-alkynoates 17 recent advances in the transition metal-catalysed asymmetric hydrosilylation of ketones, imines, and electrophilic C=C bonds 18 Michael additions catalysed by transition metals and lanthanide species 19 recent progress in asymmetric organocatalysis, including the aldol reaction, Mannich reaction, Michael addition, cycloadditions, allylation, epoxidation, and phase-transfer catalysis 20 and nucleophilic phosphine organocatalysis.21... 

Despite this tendency, examples of alkylation, acylation, sulfonylation, halogenation, silylation, and phosphorylation of aziridines at nitrogen abound. Aziridinium salts can be prepared by further alkylation of the aziridine nitrogen. Aziridines can also be alkylated on nitrogen with epoxides producing -hydroxyamines. 

JH can be inactivated by opening of the epoxide ring to a diol 45, or by hydrolysis to the free acid 47, and sometimes further by phosphorylation of the diol (Scheme 5). As the isolation and identification of enzymes involved in hormone synthesis and catabolism advances, a JH diol kinase has been isolated from the tobacco hornworm Manduca sexta that converts JH I diol into the phosphate 48.91 This enzyme is probably the first example of a phosphotransferase directly involved in the catabolism and inactivation of a lipid-soluble hormone. It was much less active in catalysing the phosphorylation of JH II or JH III diols and was inactive with the free JH acids.91... 

Epoxide Aziridine Phosphoryl/phosphonyl/ phosphinyl halide Azo... 

Mechanistic studies have been reported on the addition of alkylphosphonic acid reagents (325) to trialkyl-substituted epoxides (326). The addition occurs according to a three-step mechanism starting with rapid nucleophilic attack of the phosphorylated anion on the most alkyl-substituted carbon of oxirane, followed by formation of a dioxaphospholane structure (327) with release of... 

Reduction of iodohydrins. In Cornforth s stereospecific synthesis of a cis or irons olefin, an intermediate is a chlorohydrin of predictable configuration which cannot be reduced directly to the olefin. The conversion is accomplished by three strictly stereospeciflc steps formation of the epoxide, cleavage with HI (Nal—AcOH—EtCOgH), and reduction of the resulting iodohydrin with stannous chloride, phosphoryl chloride, and pyridine. 

Ryabov, B.V., lonin, B.L, and Petrov, A.A., Oxirane-carbonyl isomerization of phosphorylated a-halooxiranes, Zh. Obshch. Khim., 59, 272,1989 J. Gen. Chem. USSR (Engl. Transl.), 59, 233,1989. Sturtz, G., and Pondaven-Raphalen, A., Catalytic epoxidation of a,P- and P.y-unsaturated phosphonates with hydroperoxides. Bull. Soc. Chim. Fr, 125, 1983. 

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