The powerful effect of N-aryl substitution in promoting the thermal rearrangement of 5-spirocyclopropaneisoxazolidines

Authors
Cordero, FM Barile, I De Sarlo, F Brandi, A
Citation
Fm. Cordero et al., The powerful effect of N-aryl substitution in promoting the thermal rearrangement of 5-spirocyclopropaneisoxazolidines, TETRAHEDR L, 40(36), 1999, pp. 6657-6660
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
36
Year of publication
1999
Pages
6657 - 6660
Database
ISI
SICI code
0040-4039(19990903)40:36<6657:TPEONS>2.0.ZU;2-Y
Abstract
N-Alkyl 5-spirocyclopropaneisoxazolidines rearrange to tetrahydropyridone d erivatives by heating. The presence of a phenyl ring on the nitrogen atom s ignificantly reduces the rearrangement temperature. This effect is enhanced by electron-donating substituents and reduced by electron-withdrawing subs tituents on the phenyl ring. (C) 1999 Elsevier Science Ltd. All rights rese rved.