65842-25-3

Basic information

• Product Name: Oxiranepropanal
• CAS NO: 65842-25-3
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Mol File: 65842-25-3.mol

Chemical Properties

• CAS DataBase Reference: Oxiranepropanal(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranepropanal(65842-25-3)
• EPA Substance Registry System: Oxiranepropanal(65842-25-3)

Safety Data

• Hazardous Substances Data: 65842-25-3(Hazardous Substances Data)

Upstream product

• 279-35-6 1,3-epiperoxycyclopentane 
• 821-09-0 n-Pent-4-enyl alcohol 

Relevant articles and documents

Extreme rate acceleration by axial thiolate coordination on the isomerization of endoperoxide catalyzed by iron porphyrin

(Chemical Equation Presented) A coordinated effort: The isomerization mechanism of prostaglandin H2 (PGH2), which is catalytically isomerized to prostacyclin or thromboxane A2 by cytochrome P450s, was investigated using a hemethiolate complex and an endoperoxide. Isomerization of endoperoxides proceeded very rapidly with this complex, whereas imidazole- or chloride-ligated heme had slight or no catalytic activity (see scheme).

Properties of Ti-beta zeolites synthesized by dry-gel conversion and hydrothermal methods

The large-pore beta zeolite containing Ti has been synthesized in the presence of alkali cations (Na+) by a dry-gel conversion (DGC) technique using tetraethylammonium hydroxide (TEAOH) as a structure-directing agent. The obtained Ti-beta zeolites were compared with hydrothermally synthesized (HTS) Ti-beta. It was found that Ti-beta-DGC samples adsorbed less water (12-13 wt %) than Ti-beta-HTS (19 wt %), indicating that Ti-beta-DGC is more hydrophobic than Ti-beta-HTS. We propose that this leads to a higher activity for the former in the oxidation of cyclohexane. Upon being washed with H2SO4, the turnover number (TON) of DGC samples slightly increased for the oxidation of cyclohexane. DGC and HTS samples demonstrated no significant difference in the activity for oxidation reactions of unsaturated alcohols and C6-C8 cyclic alcohols.

Ruthenium(II)-Catalyzed Reactions of 1,4-Epiperoxides

The behavior of 1,4-epiperoxides in the presence of transition-metal complexes is highly dependent on the structures of the substrates and the nature of the metal catalysts.Reaction of saturated epiperoxides such as 1,3-epiperoxycyclopentane, 1,4-epiperoxycyclohexane, or dihydroascaridole catalyzed by RuCl2(PPh3)3 in dichloromethane gives a mixture of products arising from fragmentation, rearrangement, reduction, disproportionation, etc.Prostaglandin H2 methyl ester undergoes clean and stereospecific fragmentation to afford methyl(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoate and malonaldehyde.Bicyclic 2,3-didehydro 1,4-epiperoxides give the syn-1,2:3,4-diepoxides by the same catalyst.The monocyclic analogues are transformed to a mixture of diepoxides and furan products.The stereochemical outcome of the epoxide formation reflects unique differences in the ground-state geometry of the starting epiperoxide substrates.FeCl2(PPh3)2 serves as a useful catalyst for the skeletal change of sterically hindered bicyclic 2,3-didehydro 1,4-epiperoxides to the syn-diepoxides.In addition, the Fe complex best effects the conversion of 1,4-unsubstituted 2,3-didehydro epiperoxides to furans.The Ru-catalyzed reactions are interpreted in terms of the intermediacy of inner-sphere radicals formed by atom transfer of the Ru(II) species to peroxy substrates, in contrast to the Fe-catalyzed reactions proceeding via free, outer-sphere radicals generated by an electron-transfer mechanism.

CoTPP-CATALYZED REACTION OF SATURATED BICYCLIC ENDOPEROXIDES

Saturated bicyclic endoperoxides were exposed to CoTPP (Cobalt-mesotetraphenylporphyrine) in chloroform, the peroxyde bond was cleaved and a mixture of products arising from fragmentation and reduction obtained.

PHOTOLYSIS OF SATURATED BICYCLIC PEROXIDES

Under direct photolysis (n.2.1)-peroxides (n=3-5) isomerise chiefly to epoxyaldehydes, (n.2.2)-peroxides (n=2-4) mainly undergo dehydrogenation to cycloalkane-1,4-diones, and 2,3-dioxabicyclo(2.2.1)heptane exhibits both types of behaviour; photo-isomerisation of 6,7- into 6,8-dioxabicyclooctane occurs when benzophenone is present as sensitiser.