88330-51-2Relevant academic research and scientific papers
N,O-Heterocyclics. 13. Isoxazolidinium Salts as Synthons to N,N,O-Trisubstituted Hydroxylamines
Liguori, Angelo,Sindona, Giovanni,Uccella, Nicola
, p. 1207 - 1215 (2007/10/02)
Substituted izoxazolidinium salts react with lithium aluminium hydride to yield open-ring products which have hydroxylamine structures.The bimolecular reaction-mechanism has been investigated by substituent effect and the structure of the products ascertained by spectroscopic methods with the aid of the MIKE technique.The overall process of the ring-opening substitution is controlled by the polarisation of the C-N bond with steric and conformational factors acting mainly at the -5 position of the nucleus.The mechanism of isoxazolidinium ion reaction defines the use of these synthons toward the synthesis of N,N,O-trisubstituted hydroxylamines and substituted 1,3-amino-alcohols.
