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Acid hydrolysis of 2‐substituted 3‐methyl‐tetrahydro‐1,3‐oxazines: Simple models for tertiary glycosylamines
Author(s) -
Parkkinen Aija,
Pihlaja Kalevi
Publication year - 1991
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610040109
Subject(s) - chemistry , hydrolysis , heterolysis , oxazines , isopropyl , decomposition , organic chemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , polymer chemistry , combinatorial chemistry , catalysis
The hydrolytic decomposition of 2‐phenyl‐ and 2‐isopropyl‐3‐methyltetrahydro‐1,3‐oxazines to 3‐methylaminopropan‐1‐ol and appropriate aldehydes was studied by 1 H NMR and UV spectroscopy in acidic solutions. The time‐dependent spectra confirmed that the formation of the final products was preceded by an equilibration of three components, the two Schiff base intermediates and the starting material, of which the former produced a carbinolamine which in turn underwent heterolysis to the final products.