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

Riediker Martin | Zendy; Graf Walter | Zendy

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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

Author(s) -

Riediker Martin,

Graf Walter

Publication year - 1979

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19790620702

Subject(s) - chemistry , anomeric effect , conformational isomerism , stereochemistry , anomer , ether , nuclear magnetic resonance spectroscopy , molecule , organic chemistry

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 CCN bond. This finding is interpreted in terms of a generalized anomeric effect operating in the α‐cyano‐hydroxylamin‐ether structural unit.

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