PHOTOISOMERIZATION OF 2,2''-ETHANO-BRIDGED META-TERPHENYL DERIVATIVES - RING CONSTRAINT ACTIVATES AN UNREACTIVE CHROMOPHORE

被引：27

作者：

UDAYAKUMAR, BS ^{[1
]}

SCHUSTER, GB ^{[1
]}

机构：

[1] UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 01期

关键词：

D O I：

10.1021/jo00027a059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photochemistry of 2,2''-ethano-bridged m-terphenyl derivatives 4, 8, and 9 was investigated. These compounds are chiral and may be suitable photoresolvable additives to discotic liquid crystals. Unlike their unbridged analogues, 4, 8, and 9 rearrange rapidly when irradiated with UV light to the o-terphenyl compounds 10, 11, and 12, respectively. This rearrangement is likely to proceed through an intermediate benzvalene valence-bond isomer. The high reactivity of the 2,2''-ethano-bridged compounds is attributed to distortion in their lowest excited singlet states and to the relief of strain when the ortho isomers are formed.

引用

页码：348 / 352

页数：5

共 27 条

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