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1H NMR Spectroscopic Studies of the Stability of an Oxazolidine Condensation Product

✍ Scribed by Gerard P. Moloney; Magdy N. Iskander; David J. Craik

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
299 KB
Volume
35
Category
Article
ISSN
0749-1581

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✦ Synopsis

Condensation of (Γ”)-norephedrine with excess formaldehyde under mild conditions leads to formation of the 2 :1 condensation product N,NΒΊ-methylenebis(4-methyl-5-phenyl)oxazolidine compared with the reaction with 1 mol of formaldehyde, which leads to 4-methyl-5-phenyloxazolidine. 1H and 13C 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 but breaks down rapidly in to yield a 50 : 50 mixture of 4-methyl-5-phenyloxazolidine and 3-CDC1 3 CD 3 OD hydroxymethyl-4-methyl-5-phenyloxazolidine. Upon addition of to this equimolar mixture, the latter com-D 2 O pound decomposes to norephedrine and formaldehyde, whereas the former compound is stable.

1997 by John ( Wiley & Sons, Ltd.

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