ACTION DE L'EAU OXYGENEE ET DE L'ACIDE p-NITROPERBENZOIEQUE SUR DES IMINES, DES OXAZIRANNES ET DES NITRONES CYCLIQUES STEROIEDIQUES DERIVES DE LA CONANINE

Article abstract of DOI:10.1016/S0040-4020(01)92092-7

Hydrogen peroxide and a peracid react with pyrrolidinic imines, oxaziridines and nitrones of the steroidal series, to give α-hydroxylated nitrones, α-peroxyimines, hydroxylactones or hydroxamic acids.Analogies and differences between reactivities of both oxidants are shown.Thus, a peracid oxidizes a nitrone as well as an oxaziridine, whereas hydrogen peroxide which oxidizes a nitrone, by contrast, deoxygenates an oxaziridine.Differences appear also, depending on the structure of the intermediates formed which carry either hydroperoxide or perester groups.The presence of a better leaving group in the latter case may modify the course of reactions effected on a α-hydroxylated nitrone or imine.Furthermore the acylation of an aldonitrone facilitates its oxidation and leads with a peracid to an O-acylhydroxamic acid protected from further oxidation.