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Paper | Regular issue | Vol 36, No. 3, 1993, pp.585-600
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6223
Ring-Opening of 4-Isoxazolines: Competitive Formation of Enamino Derivatives and α,β-Enones

Ugo Chiacchio, Franco Casuscelli, Angelo Liguori, Antonio Rescifina, Giovanni Romeo,* Giovanni Sindona, and Nicola Uccella*

*Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, 98168 Messina, Italy


Ring-opening 3-substituted 4-isoxazolines, proceeding through the intermediate isoxazolinium salts, follows two competing reaction pathways leading to α,β-enones and enamines respectvily. The rearrangement courses can be controlled as a function of substitution pattern and experimental conditions.