ChemInform Abstract: AZOLE 92. MITT. RK. VON N‐SUBSTITUIERTEN HYDROXYLAMINEN MIT MESITYLOXID, SYNTH. VON 5‐HYDROXY‐ UND 5‐ALKOXY‐ISOXAZOLIDINEN

Abstract

Mesityloxid (III) reagiert mit dem Hydroxylamin (II) in Abhängigkeit vom pH‐ Wert entweder zu dem Hydroxyisoxazolidin (I) oder dem Methoxy‐isoxazolidin (IV) (1,4‐Addition).

A Simple Environmentally Friendly Method for the Synthesis of Hydroxyisoxazolidine Derivatives

“…For the last fifty years, there have been few articles about the synthesis of hydroxyl isoxazolidines from unsaturated carbonyl compounds and hydroxylamine (or its derivatives/analogs) [4,5,17–29] . The formation of 5‐hydroxyisoxazolidines easily occurred in neutral pH at room temperature (in rather an anhydrous condition), few examples of 3‐hydroxyisoxazolidines synthesis are also known, but only for benzohydroxyamic acid and its analogs ( p ‐NO 2 , p ‐Br and 2,3,5‐(CH 3 ) 3 ).…”

“…Formation hydroxyisoxazolidines in the reaction of enones and hydroxylamine was tested only by Belly (aliphatic enones, scheme 2) [28] and Mavrov and Firgang (aliphatic‐aromatic enones, scheme 3). [5,29] Mavrov and Firgang tested several bases and only for NaOH observed the formation of 5‐hydroxy isoxazolidine with low to moderate yield.…”