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15N NMR study of bi- and tricyclic 1,2,3,5-tetrazepin-4-ones

✍ Scribed by Bertrand J. Jean-Claude; Christopher I. Williams

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 341 KB
Volume: 36
Category: Article
ISSN: 0749-1581
DOI: 10.1002/(sici)1097-458x(199802)36:2<87::aid-omr221>3.0.co;2-e

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✦ Synopsis

The 15N NMR spectra of the novel seven-membered 1,2,3,5-tetrazepinone ring systems were studied. The chemical shift of N-2 was found to be signiÐcantly responsive to substituent changes at the phenyl ring. As the electron-withdrawing character of the substituents increased, N-2 became more deshielded. Studies on the diazotization of the 2-aminourea 6c using speciÐc labeling showed that the tetrazepinones are in equilibrium with their acyclic diazourea form 9, and that this equilibrium lies towards the formation of the 1,2,3,5-tetrazepinone at neutral or basic pH. Solid-state NMR data indicated that N-3 was signiÐcantly more delocalized in the 1,2,3-triazene moiety of the tetrazinone 2 than in the electron-deÐcient tetrazepinone 5f.

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