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

[1] PHOTOLYSIS OF N-ARYLSULPHONYL-SS-DIMETHYLSULPHOXIMIDES IN AROMATIC SOLVENTS - PHOTOISOMERISATION OF METHYLBIPHENYLS [J].

ABRAMOVITCH, RA ;

TAKAYA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (18) :1806-1809

[2] MOLECULAR-GEOMETRY AND CONFORMATIONAL STABILITY OF 4,5-DIMETHYLPHENANTHRENE AND 3,4,5,6-TETRAMETHYLPHENANTHRENE - A LOOK AT THE STRUCTURAL BASIS OF THE BUTTRESSING EFFECT [J].

ARMSTRONG, RN ;

AMMON, HL ;

DARNOW, JN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2077-2082

[3]

Billard J., 1980, Liquid Crystals of One- and Two-Dimensional Order. Proceedings of the Conference, P383

[4] NUCLEOPHILIC DISPLACEMENT IN POLYHALOGENOAROMATIC COMPOUNDS .3. KINETICS OF PROTIODEIODINATION OF IODOARENES [J].

BOLTON, R ;

SANDALL, JPB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (02) :278-280

[5] ORGANIC-PHOTOCHEMISTRY OF BENZENE .1. [J].

BRYCESMITH, D ;

GILBERT, A .

TETRAHEDRON, 1976, 32 (12) :1309-1326

[6] LIQUID-CRYSTALS OF DISC-LIKE MOLECULES [J].

CHANDRASEKHAR, S ;

SADASHIVA, BK ;

SURESH, KA .

PRAMANA, 1977, 9 (05) :471-480

[7]

CHANDRASEKHAR S, 1982, ADV LIQ CRYST, V5, P47

[8] INTRAMOLECULAR ARYLATIONS OF SOFT ENOLATES CATALYZED BY ZEROVALENT PALLADIUM [J].

CIUFOLINI, MA ;

QI, HB ;

BROWNE, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4149-4151

[9]

DESTRADE H, 1983, J CHIM PHYS, P137

[10]

FUFII T, 1984, CHEM PHYS LETT, V111, P350

← 1 2 3 →