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Yaremenko, Ivan A.; Fomenkov, Dmitri I.; Budekhin, Roman A.; Radulov, Peter S.; Medvedev, Michael G.; Krivoshchapov, Nikolai V.; He, Liang-Nian; Alabugin, Igor V.; Terent’ev, Alexander O.
Journal of organic chemistry, 04/2024, Letnik: 89, Številka: 8Journal Article
Four heteroatoms dance in the cascade of four pericyclic reactions initiated by ozonolysis of CN bonds. Switching from imines to semicarbazones introduces the fifth heteroatom that slows this dance, delays reaching the thermodynamically favorable escape path, and allows efficient interception of carbonyl oxides (Criegee intermediates, CIs) by an external nucleophile. The new three-component reaction of alcohols, ozone, and oximes/semicarbazones greatly facilitates synthetic access to monoperoxyacetals (alkoxyhydroperoxides).
