Tetrahedron p. 9473 - 9482 (1992)
Update date:2022-08-04
Topics:
Chiacchio, Ugo
Liguori, Angelo
Romeo, Giovanni
Sindona, Giovanni
Uccella, Nicola
High yield conversion of 3-aryl-5-ethoxy-isoxazolidines into 3-styryl nitrones has been achieved by 1,5 h refluxing in aq. H2SO4 or catalytic p-toluensulfonic acid/ethanol media. The rearrangement pathway is interpretable on the basis of the ring-opening process of intermediate 5-hydroxy-isoxazolidines. Formation of a masked 5-OH function has been also developed by basic or acid treatment of 5-acetoxy-isoxazolidines.
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Doi:10.1016/j.tet.2013.08.020
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(2013)
