Interrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds

Авторы: 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.
Журнал: Journal of Organic Chemistry
Год издания: 2024
Издательство: American Chemical Society
Местоположение издательства: United States
DOI: 10.1021/acs.joc.4c00233
Аннотация: Four heteroatoms dance in the cascade of four pericyclic reactions initiated by ozonolysis of C═N 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).
Добавил в систему: Будехин Роман Алексеевич

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