1393814-46-4Relevant academic research and scientific papers
Mechanistic insights into the rearrangement of azetidine N-oxides to isoxazolidines
Menguy, Laurence,Drouillat, Bruno,Marrot, Jérome,Couty, Fran?ois
supporting information; experimental part, p. 4697 - 4699 (2012/09/10)
Various functionalized azetidines were oxidized with mCPBA or hydrogen peroxide, to produce the corresponding N-oxide and study its fate in the [1,2] Meisenheimer rearrangement. This ring expansion leading to isoxazolidines occurs readily, without trapping of the transient N-oxide. Starting with azetidines bearing a nitrile or an ester group at C-2, the rearrangement is regioselective. However, a varying amount of epimerization on the migrating radical is observed, which can also be observed with the related [1,2] Stevens rearrangement.
