High yield conversion of 3,5,5-triarylisoxazolidines into indene derivatives has been achieved by 4 h refluxing in aq. H2SO4. The rearrangement pathway is interpretable on the basis of a ring-opening process where the crucial step is the protonation of the oxygen atom of the isoxazolidine nucleus. MNDO calculations performed on N,N,O-trimethylhydroxylamine chosen as model system support the proposed mechanism.
RING-OPENING OF SUBSTITUTED ISOXAZOLIDINES - ONE-POT SYNTHESIS OF INDENES
CHIACCHIO, Ugo;
1993-01-01
Abstract
High yield conversion of 3,5,5-triarylisoxazolidines into indene derivatives has been achieved by 4 h refluxing in aq. H2SO4. The rearrangement pathway is interpretable on the basis of a ring-opening process where the crucial step is the protonation of the oxygen atom of the isoxazolidine nucleus. MNDO calculations performed on N,N,O-trimethylhydroxylamine chosen as model system support the proposed mechanism.File in questo prodotto:
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