Calcium peroxide diperoxohydrate as a storable chemical generator of singlet oxygen for organic synthesis |
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Authors: | Pierlot Christel Nardello Véronique Schrive Jordane Mabille Caroline Barbillat Jacques Sombret Bernard Aubry Jean-Marie |
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Institution: | LCOM, Equipe "Oxydation et Formulation", ESA CNRS 8009, ENSCL, BP 108, F-59 652 Villeneuve d'Ascq Cedex, France. |
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Abstract: | Calcium peroxide diperoxohydrate (CaO(2).2H(2)O(2)) is an environmentally friendly generator of singlet oxygen ((1)O(2), (1)Delta(g)) that can be used in organic synthesis as an alternative to the regular photochemical method. This compound produces (1)O(2) in various solvents and can be easily recovered by filtration for further regeneration. Both monitoring of (1)O(2) luminescence at 1270 nm and specific trapping have shown that CaO(2).2H(2)O(2) can be stored for several days at -80 degrees C and that the yield of (1)O(2) 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. |
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