CONFORMATIONAL STUDY OF THE 4,9-DIHETERO-(Z,Z)-CYCLODECA-1,6-DIENE RING-SYSTEM - THE MONO-BENZO AND DI-BENZO ANALOGS

被引：7

作者：

KLEINPETER, E

HARTMANN, J

SCHROTH, W

机构：

[1] Sektion Chemie, Martin-Luther-Universität Halle-Wittenberg, Halle (Saale), DDR-4050

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 1990年 / 28卷 / 07期

关键词：

!sup]13[!/sup]C NMR; !sup]1[!/sup]H NMR; 4,9‐Dihetero‐(Z,Z)‐cyclodeca‐1,6‐dienes; Restricted rotation; Ring inversion barriers;

D O I：

10.1002/mrc.1260280713

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The dynamic 1H and 13C NMR spectra of a series of mono‐ and bis‐annelated 4,9‐dihetero‐(Z,Z)‐cyclodeca‐1,6‐dienes were obtained and are discussed with respect to ground‐state conformers and the barriers to ring inversion, and to the restricted rotation about exocyclic partial C,N double bonds. The ten‐membered rings are, with one exception, anancomeric chair conformers and interconvert via a combination of single bond rotations and bond angle bendings. Depending on the heteroatoms present, the series of decreasing barriers to ring inversion S > NH > O was obtained. Benzannelation decreases the free energy of activation of the same dynamic process owing to greater intramolecular transannular H,H interactions. Copyright © 1990 John Wiley & Sons, Ltd.

引用

页码：628 / 634

页数：7

共 28 条

[1] 1,6-DIOXACYCLODECA-3,8-DIENE [J].