INTRAMOLECULAR PHOTOCYCLOADDITION OF 4-PHENOXYBUT-1-ENES - A CONVENIENT ACCESS TO THE 4-OXATRICYCLO[7.2.0.0(3,7)]UNDECA-2,10-DIENE SKELETON

被引：29

作者：

ALQARADAWI, SY ^{[1
]}

COSSTICK, KB ^{[1
]}

GILBERT, A ^{[1
]}

机构：

[1] UNIV READING,DEPT CHEM,POB 224,READING RG6 2AD,BERKS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 09期

关键词：

D O I：

10.1039/p19920001145

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photochemistry of 4-phenoxybut-1-ene is markedly influenced by the presence and position of electron-withdrawing substituents on the benzene ring. A cyano substituent in the 2'- or 4'-position promotes an efficient intramolecular cycloaddition to give good yields of the 4-oxatricyclo-[7.2.0.0 3,7]undeca-2,10-dienes, by way of the photolabile 11-oxabicyclo[6.3.0]undeca-1,3,5-triene, the precursor of which is presumed to be a thermally labile intramolecular ortho photocycloadduct. The 3'-cyano isomer reacts inefficiently and only the 2'-isomer in the methoxycarbonyl series undergoes the photocycloaddition. The formation of the trienes is efficiently quenched by 1,3-dienes but their intramolecular cyclisation is unaffected by the presence of the triplet quenchers.

引用

页码：1145 / 1148

页数：4

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