22460-95-3Relevant articles and documents
Ozone as an Oxygen Source for Alkene Ene-Reactions
Falk, H.,Leimhofer, J.
, p. 85 - 90 (1995)
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.
“Dark” Singlet Oxygen Made Easy
Elsherbini, Mohamed,Allemann, Rudolf K.,Wirth, Thomas
supporting information, p. 12486 - 12490 (2019/08/26)
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.
Dark singlet oxygenation of β-citronellol: A key step in the manufacture of rose oxide
Alsters, Paul L.,Jary, Walther,Nardello-Rataj, Veronique,Aubry, Jean-Marie
experimental part, p. 259 - 262 (2010/06/13)
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.