10496-80-7Relevant academic research and scientific papers
Calcium peroxide diperoxohydrate as a storable chemical generator of singlet oxygen for organic synthesis
Pierlot, Christel,Nardello, Veronique,Schrive, Jordane,Mabille, Caroline,Barbillat, Jacques,Sombret, Bernard,Aubry, Jean-Marie
, p. 2418 - 2423 (2002)
Calcium peroxide diperoxohydrate (CaO2·2H2O2) is an environmentally friendly generator of singlet oxygen (1O2, 1Δg) that can be used in organic synthesis as an alternative to the regular photochemical method. This compound produces 1O2 in various solvents and can be easily recovered by filtration for further regeneration. Both monitoring of 1O2 luminescence at 1270 nm and specific trapping have shown that CaO2·2H2O2 can be stored for several days at -80 °C and that the yield of 1O2 is equal to 25%. Oxidation of typical organic substrates in methanol or THF through [4 + 2] or [2 + 2] cycloaddition and ene reaction have been carried out on a preparative scale with total conversion and selectivity.
Oxidation of Tetraarylselenophenes and Benzoselenophene with m-Chloroperbenzoic Acid
Nakayama, Juzo,Matsui, Tomoki,Sato, Noriko
, p. 485 - 486 (1995)
Oxidation of tetraarylselenophenes with m-chloroperbenzoic acid produces cis-1,2-diaroyl-1,2-diarylethylenes and SeO2 as the principal product, while the oxidation of benzoselenophene affords benzoselenophene 1-oxide.
High-efficiency microphotooxidation using milliwatt LED sources
Carney, John M.,Hammer, Reagan J.,Hulce, Martin,Lomas, Chad M.,Miyashiro, Dayna
, p. 352 - 355 (2011)
Inexpensive milliwatt light emitting diode (LED) sources allow energy- and atom-efficient microphotochemical reactions. Thus, sources constructed from three 120 mW 5 mm diameter 627 nm LED's enable μmol-mmol scale methylene blue-sensitized singlet oxygen photooxidations of various arenes and cyclopentadienones using a 3-5 M excess of oxygen in 82-98% yields.
Studies on Singlet Oxygen in Aqueous Solution. Part 1. Formation of Singlet Oxygen from Hydrogen Peroxide with Two-electron Oxidants
Evans, Dennis F.,Upton, Mark W.
, p. 1141 - 1145 (1985)
Kinetic parameters are reported for the trapping of singlet oxygen by anthracene-9,10-bis(ethanesulphonate) (aes) in water and deuterium oxide solutions.The kinetics of the reactions of N-chlorosuccinimide, chloramine T (N-chlorotoluene-p-sulphonamide), N-chloromethanesulphonamide, and N,N-dichloromethanesulphonamide with hydrogen peroxide have been studied.For chloramine T and N-chloromethanesulphonamide the rate-determining step is formation of the corresponding dichloro-compounds, which are the reactive species.Using aes as a trap, it is shown that both chloramine T and N-chlorosuccinimide with H2O2 produce singlet oxygen in essentially quantitative yield.Iodylbenzene reacts with H2O2 to give, in the rate-determining step, iodosylbenzene and oxygen and then iodobenzene and oxygen; 47 percent of the oxygen produced is in the singlet state.For the corresponding reaction with 4-iodosylbenzene-1-sulphonic acid, the yield of singlet oxygen is 45 percent, i.e. indistinguishable within experimental error.Periodate and H2O2 give lower yields of singlet oxygen, and it is considered that two concomitant processes are involved.With hypobromite and H2O2 the yield of singlet oxygen is 76 percent.These variations in yield are briefly discussed.
Visible-light-mediated oxidative dimerization of arylalkynes in the open air: Stereoselective synthesis of (Z)-1,4-enediones
Wei, Donglei,Liang, Fushun
supporting information, p. 5860 - 5863 (2016/11/29)
An organic photoredox catalytic one-pot protocol is developed for the highly stereoselective synthesis of (Z)-1,4-enediones. The reaction starts directly from alkyne precursors, using 4-(4-cyanophenyl)-2,6-diphenylpyrylium tetrafluoroborate (CN-TPT) as an efficient photosensitizer and dioxygen in the air as a green oxidant. A Csp-Csp oxidative coupling/[4 + 2] cyclization (with dioxygen)/fragmentive isomerization cascade mechanism was proposed. The predominant formation of (Z)-1,4-enediones is attributed to the efficient visible-light illumination from blue LEDs, along with possible energy transfer from the photosensitizer CN-TPT to the E-isomers.
Microphotochemistry using 5-mm light-emitting diodes: Energy-efficient photooxidations
Carney, John M.,Hammer, Reagan J.,Hulce, Martin,Lomas, Chad M.,Miyashiro, Dayna
experimental part, p. 2560 - 2566 (2012/09/07)
Commercial, inexpensive 5-mm milliwatt light-emitting diodes are effective sources for batch microphotochemical oxidations. Using limited quantities of singlet oxygen, these oxidations are atom economical and therefore useful for labeling experiments with rare isotopes. Georg Thieme Verlag Stuttgart · New York.
Oxidation of aromatic compounds: XVII. Oxidative cross-dimerization of diarylacetylenes in the system CF3CO2H-CH 2Cl2-PbO2. Characteristic of cation-radicals of diarylacetylenes by cyclic voltammetry and ESR spectroscopy
Vasil'ev,Rudenko
experimental part, p. 1282 - 1289 (2010/12/19)
The oxidation of mixtures of diarylacetylene ArC≡CAr and Ar′C≡CAr′ in a system CF3CO2H-CH 2Cl2-PbO2 (0°C, 1.5 h) results in products of cross-dimerization, (Z)-1,2,3,4-tetraarylbut-2-ene-1,4-diones Ar(ArCO) C=C(COAr′)Ar′. The routes of transformation of intermediate cation-radicals of diarylacetylenes [ArC≡CAr]+? into the final products of oxidative dimerization are elucidated. By cyclic voltammetry and ESR spectroscopy the high reactivity of the diarylacetylene cation-radicals is demonstrated, the character of their singly occupied molecular orbitals (a2 or b1) has been revealed by ESR method.
Synthesis of tetrasubstituted furans via sequential Pd(OAc) 2/Zn(OTf)2-catalyzed oxidation and cydization of aromatic alkynes with molecular oxygen
Wang, Azhong,Jiang, Huanfeng,Xu, Qiuxiang
scheme or table, p. 929 - 932 (2009/09/29)
The development of a new method for the synthesis of tetrasubstituted furans using aromatic alkynes is reported. The strategy involves a tandem process of palladium-catalyzed oxidation and Zn(OTf)2-catalyzed cyclization in the presence of molecular oxygen.
Thermal oxidation of tetracyclones (2,3,4,5-tetraarylcyclopentadienones)
Thiemann, Thies,Iniesta, Jesus,Walton, David J.
experimental part, p. 173 - 180 (2009/05/07)
Tetracyclones are transformed to a mixture of diacylstilbenes and a-pyrones, when they are heated in diphenylether saturated with oxygen.
Iron (III) perchlorate adsorbed on silica gel: A reagent for organic functional group transformations
Parmar, Anupama,Kumar, Harish
, p. 2301 - 2308 (2008/02/10)
Adsorption of Fe(ClO4)3(H2O)6 onto chromatographic-grade silica gel in the presence of organic solvents (S=water, acetonitrile, or lower fatty acids) produces a supported reagent, Fe(ClO4)3(S)6/SiO2. This reagent has been found to be effective for the rapid organic functional group transformations such as dimerization of alkynes, aromatic hydrocarbons, selective oxidation of thiols to disulfides, and transannular reactions in 1,5-cyclooctadienes on grinding using pestle and mortar in the solid state. Copyright Taylor & Francis Group, LLC.
