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1,3-Diaxial Repulsion vs. π-Delocalization in the 7-Amino-2,4-diazabicyclo[3.3.1]nonan-3-one Skeleton

✍ Scribed by Michael Weber; Bernd Morgenstern; Kaspar Hegetschweiler; Helmut W. Schmalle

Publisher
John Wiley and Sons
Year
2001
Tongue
German
Weight
103 KB
Volume
84
Category
Article
ISSN
0018-019X

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✦ Synopsis

6,

8,

nonan-7-ammonium chloride hydrate (3Cl H2 O) and (1R,5S,6S,8R)- 7-amino-6,8,9-trihydroxy-2,4-diazabicyclo[3.3.1]nonan-3-one (4) have been prepared, and their crystal structures have been determined from single-crystal X-ray diffraction data. Both compounds consist of a bicyclic skeleton with the three N-atoms in an all-cis-1,3,5-triaxial arrangement. Considerable repulsion between these axial N-atoms is indicated by a significant distortion of the two cyclohexane chairs and by increased N ´´´N distances. The lone pair of the free amino group of 4 is involved in intermolecular Hbonding and is turned away from the adjacent carbonyl C-atom of the urea moiety. The structural properties together with the observed reactivity do not provide any evidence for an intramolecular donor-acceptor interaction between the carbonyl C-and the amine N-atom.

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✍ Victor V. Dotsenko; Sergey G. Krivokolysko; Victor P. Litvinov 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 19 KB 👁 1 views

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