Mechanistic insights into the rearrangement of azetidine N-oxides to isoxazolidines |
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Authors: | Laurence MenguyBruno Drouillat Jérome MarrotFrançois Couty |
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Institution: | Institut Lavoisier, Université de Versailles St. Quentin-en-Yvelines, UMR 8180, 45 Avenue des Etats-Unis, 78035 Versailles, France |
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Abstract: | 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. |
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Keywords: | Azetidines [1 2] Meisenheimer rearrangement Isoxazolidines N-oxides |
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