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1 H NMR Spectroscopic Studies of the Stability of an Oxazolidine Condensation Product
Author(s) -
Moloney Gerard P.,
Iskander Magdy N.,
Craik David J.
Publication year - 1997
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199705)35:5<337::aid-omr86>3.0.co;2-5
Subject(s) - chemistry , oxazolidine , formaldehyde , condensation , hydroxymethyl , yield (engineering) , proton nmr , nuclear magnetic resonance spectroscopy , carbon 13 nmr , organic chemistry , decomposition , condensation reaction , polymer chemistry , medicinal chemistry , catalysis , physics , materials science , metallurgy , thermodynamics
Condensation of (–)‐norephedrine with excess formaldehyde under mild conditions leads to formation of the 2:1 condensation product N , N ′‐methylenebis(4‐methyl‐5‐phenyl)oxazolidine compared with the reaction with 1 mol of formaldehyde, which leads to 4‐methyl‐5‐phenyloxazolidine. 1 H and 13 C NMR spectroscopy was used to monitor the stability of this compound and its decomposition products. The 2:1 condensation product is found to be stable in CDC1 3 but breaks down rapidly in CD 3 OD to yield a 50:50 mixture of 4‐methyl‐5‐phenyloxazolidine and 3‐hydroxymethyl‐4‐methyl‐5‐phenyloxazolidine. Upon addition of D 2 O to this equimolar mixture, the latter compound decomposes to norephedrine and formaldehyde, whereas the former compound is stable. © 1997 by John Wiley & Sons, Ltd.