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

A Hassner, B Amit, V Marks…

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

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被引用次数: 4

摘要

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 ...