UNUSUAL TRANSFORMATION OF TRIMETHYLSILYLOXYISOXAZOLIDINES INITIATED BY THE FLUORIDE-ION

Authors
MOISEENKOV AM BELYANKIN AV BUEVICH AV VESELOVSKY VV
Citation
Am. Moiseenkov et al., UNUSUAL TRANSFORMATION OF TRIMETHYLSILYLOXYISOXAZOLIDINES INITIATED BY THE FLUORIDE-ION, Russian chemical bulletin, 43(3), 1994, pp. 420-423
Citations number
8
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
43
Issue
3
Year of publication
1994
Pages
420 - 423
Database
ISI
SICI code
1066-5285(1994)43:3<420:UTOTIB>2.0.ZU;2-8
Abstract
It was found that opening of the isoxazolidine ring of 6a alpha-isopro penyl-1 alpha/beta- trimethylsilyloxy-3,3a alpha,4,5,6,6a-hexahydro-(1 H)- cyclopent[c]isoxazoles by the F- ion initially gives an intermedia te, a tertiary nitrosocompound detected by UV and NMR spectroscopy. It s transformation, finally, into alpha,beta-unsaturated aldoximes proba bly involves an unprecedented allylic migration of the nitroso group.