Ring-opening of isoxazolidine system: Homologation of 3-aryl into 3-styryl nitrones via intermediate 5-hydroxy-isoxazolidines

DOI: 10.1016/S0040-4020(01)88315-0

Source and publish data:

Tetrahedron p. 9473 - 9482 (1992)

Update date:2022-08-04

Topics:

Authors:

Chiacchio, Ugo

Liguori, Angelo

Romeo, Giovanni

Sindona, Giovanni

Uccella, Nicola

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Article abstract of DOI:10.1016/S0040-4020(01)88315-0

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.

Full text of DOI:10.1016/S0040-4020(01)88315-0

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