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.
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
LIGUORI, Angelo;SINDONA, Giovanni;
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
