THROUGH-BOND TRANSMISSION OF POLAR SUBSTITUENT EFFECTS IN THE BICYCLO-[2.2.2]OCTANE RING-SYSTEM AS MONITORED BY SN-119 NMR CHEMICAL-SHIFTS - A SN-119 NMR-STUDY OF 10-SUBSTITUTED 9-TRIMETHYLSTANNYLTRIPTYCENES

被引：6

作者：

ADCOCK, W

IYER, VS

机构：

[1] School of Physical Sciences, Flinders University of South Australia, Adelaide

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 1991年 / 29卷 / 04期

关键词：

SN-119 SUBSTITUENT CHEMICAL SHIFTS; 10-SUBSTITUTED-9-TRIMETHYLSTANNYLTRIPTYCENES; POLAR SUBSTITUENT EFFECTS; THROUGH-BOND TRANSMISSION;

D O I：

10.1002/mrc.1260290416

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of 10-substituted(X)-9-trimethylstannyltriptycenes (2a) were synthesized and characterized and the Sn-119 chemical shifts measured. Comparisons were made of the Sn-119 substituent chemical shifts (SCS) of 2a and the corresponding values of 4-substituted(X)bicyclo[2.2.2] oct-1-yltrimethylstannanes (1a), which confirm the previous conclusion that 'through-three-bond' effects or double-hyperconjugation strongly regulate the Sn-119 shifts of the latter system. A more restricted series of 10-substituted(X)-9-methyltripycenes (2c) were acquired and their (CH3)-C-13 SCS compared with those of the corresponding bicyclo[2.2.2]octanes (1c). Significant 'through-bond' contributions are also indicated for the latter system.

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页码：381 / 386

页数：6

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