Ozone as an Oxygen Source for Alkene Ene-Reactions
A strategy was developed which uses the adduct of ozone and triphenyl phosphite as a substitute for photochemically generated singlet oxygen in ene reactions of olefins.The resulting allylic hydroperoxide can be conveniently reduced by a second mole of phosphite to yield the corresponding allylic alcohol.The aryl phosphate produced as the by-product can either be recycled by reduction or used itself as a commodity.As an example, the two key steps of the rose oxide synthesis involving singlet oxygen can thus be reduced to a one pot procedure.With respect to the reaction mechansim, additional arguments for the direct reaction of the olefin with the phoshite ozonide were gathered.A simple decomposition of the ozonide to produce singlet oxygen was made rather unlikely. - Keywords: Ene reaction; Phosphite ozonide; Organic phosphate; Rose oxide.
The present invention relates to novel compounds and their use as fragrance materials.
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(2021/06/04)
“Dark” Singlet Oxygen Made Easy
An operationally simple continuous flow generator of “dark” singlet oxygen has been developed. The singlet oxygen was efficiently reacted with several chemical traps to give the corresponding oxygenated products in high yields. The developed “dark” singlet oxygen generator has been successfully applied in the synthesis of the antimalarial drug artemisinin.
Elsherbini, Mohamed,Allemann, Rudolf K.,Wirth, Thomas
supporting information
p. 12486 - 12490
(2019/08/26)
Highly efficient continuous flow reactions using singlet oxygen as a "Green" reagent
Described is a new method for the efficient in situ production of singlet oxygen in a simple continuous flow photochemical reactor. The extremely large interfacial area generated by running the biphasic mixture in a narrow channel at a high flow rate ensures high throughput as well as fast and efficient oxidation of various alkenes, 1,3-dienes, and thioethers on a preparative scale.
Levesque, Francois,Seeberger, Peter H.
supporting information; experimental part
p. 5008 - 5011
(2011/12/04)
Dark singlet oxygenation of β-citronellol: A key step in the manufacture of rose oxide
We describe the development of a scalable process for the "dark" singlet oxygenation of β-citronellol as a key step in the manufacture of the fragrance compound, rose oxide. This process, based on catalytic disproportionation of hydrogen peroxide into singlet oxygen and water, has been carried out on production scale in 10 m3 reactors.
Alsters, Paul L.,Jary, Walther,Nardello-Rataj, Veronique,Aubry, Jean-Marie
experimental part
p. 259 - 262
(2010/06/13)
Cleaner continuous photo-oxidation using singlet oxygen in supercritical carbon dioxide
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Bourne, Richard A.,Han, Xue,Poliakoff, Martyn,George, Michael W.
experimental part
p. 5322 - 5325
(2009/10/24)
A PhSeCl-mediated allylic oxidation of prenyl moiety: A convenient method for the construction of 3-isopenten-2-ol unit
A phenylselenenyl chloride (PhSeCl)-mediated allylic oxidation to give allylically rearranged alcohol has been developed. A possible mechanism for the present reaction is generation of allylic selenide from prenyl moiety via [1,3]-sigmatropic rearrangement, followed by oxidation and [2,3]-sigmatropic rearrangement to afford 3-isopenten-2-ol.
Glycol-modified molybdate catalysts for efficient singlet oxygen generation from hydrogen peroxide
Pretreatment of molybdate-exchanged layered double hydroxides in polyalcohols such as ethylene glycol affords heterogeneous catalysts showing largely improved oxidant efficiency compared to the unmodified materials. The Royal Society of Chemistry.
Wahlen, Joos,De Vos, Dirk,Jary, Walther,Alsters, Paul,Jacobs, Pierre
p. 2333 - 2335
(2008/02/11)
PROCESS FOR THE OXIDATION OF ORGANIC SUBSTRATES BY MEANS OF SINGLET OXYGEN AT HIGH REACTION TEMPERATURES
Process for the oxidation of organic substrates by means of singlet oxygen, in which organic substrates which react with 1O2 are admixed with 10-70% strength H2O2 in an organic solvent in the presence of a molybdenum-based catalyst at a pH of 9 - 14 and a temperature in the range from 500C to the reflux temperature, whereupon the oxidation to the corresponding oxidation products occurs subsequent to the catalytic decomposition of H2O2 into water and 1O2.
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Page/Page column 7-8; 10
(2008/06/13)
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