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Unambiguous structural characterization of hydantoin reaction products using 2D HMBC NMR spectroscopy

✍ Scribed by Mary M. Senior; Tze-Ming Chan; Guoqing Li; Ying Huang; Andrew Stamford

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
227 KB
Volume
45
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Data from two‐dimensional (2D) NMR experiments were used to identify the reaction products resulting from the opening of pyroglutamates with isocyanates or thioisocyanates. The reaction has the potential to produce compounds that would have very similar one–dimensional proton (^1^H) or carbon–13 (^13^C) NMR spectra. Careful analysis of ^1^H^1^H COSY, ^1^H^1^H NOESY, and HMBC data, including chemical shifts and coupling constants, were used to distinguish correctly between carbamoyl‐2‐pyrrolidinone, hydantoin, and perhydro‐1,3‐diazepine‐2,4‐dione type structures that could result from this reaction. This work describes their preparation and subsequent identification using 2D NMR spectroscopy, and includes complete ^13^C assignments of the reaction products. The 2D NMR techniques and analysis described here can be applied successfully to other synthetic reactions with the potential to produce isomeric products. Copyright © 2007 John Wiley & Sons, Ltd.

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