Premium
N,O ‐heterocyclics. 13 . Isoxazolidinium salts as synthons to N,N, O ‐trisubstituted hydroxylamines
Author(s) -
Liguori Angelo,
Sindona Giovanni,
Uccella Nicola
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200514
Subject(s) - chemistry , synthon , steric effects , lithium aluminium hydride , yield (engineering) , ring (chemistry) , hydroxylamine , substituent , medicinal chemistry , lithium (medication) , stereochemistry , organic chemistry , medicine , materials science , metallurgy , endocrinology
Substituted isoxazolidinium 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 CN bond with steric and conformational factors acting mainly at the C‐5 position of the nucleus. The mechanism of isoxazolidinium ion reaction defines the use of these synthons towards the synthesis of N,N,O ‐trisubstituted hydroxylamines and substituted 1,3‐amino‐alcohols.