An environmentally benign procedure for the synthesis of vicinal nitrohydrins via the regioselective ring opening reaction of epoxides with nitrite anion using silica-bound 3-{2-[poly(ethylene glycol)]ethyl}-substituted 1-methyl-1H-imidazol-3-ium bromide as an effective heterogeneous phase transfer catalyst was described. Short reaction time, high yield of products, simple work-up proc...

The optimal conditions for regio- and stereoselective epoxide ring opening of N,N-disubstituted 1,2-epoxy-3-aminocyclopentanes by different nucleophilic reagents have been developed. The substituents on the nitrogen atom in the epoxide precursor and the orientation of the oxirane ring are crucial for the reaction outcome. Thus, treatment of (1RS,2SR,3SR)-1,2-epoxy-3-(N,N-dibenzylamino)cyclopent...

In this study, β-cyclodextrin(β-CD) supported, hydroxyapatite encapsulated γ-Fe2O3 (γ-Fe2O3@HAp@β-CD) was successfully prepared and evaluated as a solid-liquid phase transfer catalyst and also a molecular host system and nanoreactor for the nucleophilic ring-opening of epoxides in water for the preparation of β-azido alcohols, β-nitro alcohols, an...

Catalytic coupling of carbon dioxide with epoxides to obtain cyclic carbonates is an important reaction that has been receiving renewed interest. In this contribution, the cycloaddition reaction in the presence of various hydrogen bond donors (HBDs) catalyzed by hydroxyl/carboxyl task-specific ionic liquids (ILs) is studied in detail. It was found that the activity of ILs could be significantly...

We have examined the selectivity of rat liver microsomal epoxide hydrolase (EC 3.3.2.3) toward all of the possible positional isomers of benzo-ring diol epoxides and tetrahydroepoxides of benz[a]anthracene, as well as the 1,2-diol 3,4-epoxides of triphenylene. This set includes compounds with no bay region in the vicinity of the benzo-ring, a bay-region diol group, a bay-region epoxide group, a...

The ring-opening copolymerization of epoxides with isothiocyanates (ITCs) is explored for the first time. In presence phosphazenium benzoxide, investigated in this work including propylene oxide, ethylene and cyclohexene oxide were successfully copolymerized both an aromatic ITC, phenyl isothiocyanate, two aliphatic ITCs, ethyl isothiocyanate hexyl isothiocyanate. Effects phosphazene bases used...

Biological transformations of polyunsaturated fatty acids often lead to chemically unstable products, such as the prostaglandin endoperoxides and leukotriene A(4) epoxide of mammalian biology and the allene epoxides of plants. Here, we report on the enzymatic production of a fatty acid containing a highly strained bicyclic four-carbon ring, a moiety known previously only as a model compound for...

Rhodium-catalyzed transannulation of 1,2,3-triazoles and ring-opening reactions of epoxides is described. A number of 3,4-dihydro-2H-1,4-oxazines are obtained in moderate yields probably involving generation of α-imino rhodium(II) carbene species.

Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.

Fullerene epoxides, C₆₀O(n), having epoxide groups directly attached to the fullerene cage, constitute an interesting class of fullerene derivatives. In particular, the chemical transformations of fullerene epoxides are expected to play an important role in the development of functionalized fullerenes. This is because such transformations can readily afford a variety of mono- or polyfunctionali...