On the Conformation of 8??Membered Ring Heterocycles–Dynamic and Static Conformational Analysis of Acylated Hexahydrobenzazocines

A Hassner, B Amit, V Marks…

Index: Hassner, Alfred; Amit, Boaz; Marks, Vered; Gottlieb, Hugo E. European Journal of Organic Chemistry, 2006 , # 5 p. 1256 - 1261

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Citation Number: 4

Abstract

Abstract A high-field NMR analysis of several acylated hexahydrobenzazocines indicates that, surprisingly, ring methylene groups are typically diastereotopic at room temperature, as the barriers for the process of enantiomerization of the eight-membered ring are much higher than expected. It is shown that ring inversion is correlated (but not concerted) with rotation of the amide moiety, as the carbonyl is forced out of conjugation with the nitrogen ...