RING-OPENING OF SUBSTITUTED ISOXAZOLIDINES - ONE-POT SYNTHESIS OF INDENES

Authors
CASUSCELLI F CHIACCHIO U LIGUORI A ROMEO G SINDONA G UCCELLA N
Citation
F. Casuscelli et al., RING-OPENING OF SUBSTITUTED ISOXAZOLIDINES - ONE-POT SYNTHESIS OF INDENES, Tetrahedron, 49(23), 1993, pp. 5147-5152
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
23
Year of publication
1993
Pages
5147 - 5152
Database
ISI
SICI code
0040-4020(1993)49:23<5147:ROSI-O>2.0.ZU;2-9
Abstract
High yield conversion of 3,5,5-triarylisoxazolidines into indene deriv atives has been achieved by 4 h refluxing in aq. H2SO4. The rearrangem ent pathway is interpretable on the basis of a ring-opening process wh ere the crucial step is the protonation of the oxygen atom of the isox azolidine nucleus. MNDO calculations performed on N,N,O-trimethylhydro xylamine chosen as model system support the proposed mechanism.