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Synthetische Verwendung von Epoxynitronen. III. Der anomere Effekt als bestimmender Faktor für die Konformation der 3-Cyano-perhydro-1,2-benzoxazine

✍ Scribed by Martin Riediker; Walter Graf


Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
364 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis


The anomeric effect as a conformation determining factor for 3‐cyano‐perhydro‐1,2‐benzoxazines

An unusual population of conformer II is found by ^1^H‐NMR. spectroscopy in the conformation equilibrium I⇄ II of 1b (Fig. 3) in which the non‐bonding nitrogen electronpair is anti‐periplanar to the CCN bond. This finding is interpreted in terms of a generalized anomeric effect operating in the α‐cyano‐hydroxylamin‐ether structural unit.