N,O-HETEROCYCLICS-12. FACILE RING OPENING OF SOME ISOXAZOLIDINIUM IONS

Article abstract of DOI:10.1016/S0040-4020(01)91845-9

Substituted isoxazolidinium salts react with LiAlH4 to yield ring opened hydroxylamines.The novel bimolecular reaction mechanism has been investigated by deuterium labelling and the structure of the products ascertained by spectroscopic methods with the aid of the MIKE technique.The overall process can be defined as a ring-opening substitution, wich is controlled by steric and conformational factors that tend to prevent the alternative Hofmann-like degradation of the salts.