PHOTOLYSIS OF CYCLIC ENOL ESTERS IN THE PRESENCE OR ABSENCE OF A SINGLE ELECTRON-TRANSFER PHOTOSENSITIZER

被引：11

作者：

CLIMENT, MJ

GARCIA, H

IBORRA, S

MIRANDA, MA

PRIMO, J

机构：

[1] UNIV POLITECN VALENCIA,ETSII,DEPT QUIM,APARTADO 22012,E-46071 VALENCIA,SPAIN

[2] UNIV POLITECN VALENCIA,CSIC,INST TECHNOL QUIM,E-46071 VALENCIA,SPAIN

来源：

TETRAHEDRON | 1991年 / 47卷 / 44期

关键词：

D O I：

10.1016/S0040-4020(01)96217-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photochemistry of enol esters 1 is dominated by electrocyclic ring opening (1b --> 3 + 4), 1,3-acyl migration (1c,d --> 6c,d) and [2 + 2] dimerization (1d --> 11). Photosensitization with triphenylpyrylium tetrafluoroborate (TPT) enhances formation of oxidation products (1b --> 5, 1c,d --> 9c,d + 10c,d), presumably through the intermediacy of radical cations 1b-d+.

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收藏

页码：9289 / 9296

页数：8

相关论文

共 20 条

[1] WAGNER-MEERWEIN REARRANGEMENTS OF RADICAL CATIONS GENERATED BY TRIPHENYLPYRYLIUM TETRAFLUOROBORATE PHOTOSENSITIZED ELECTRON-TRANSFER OF AZOALKANES [J].

ADAM, W ;

DORR, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1570-1572

[2] GENERATION OF THE 1,4-DIPHENYLCYCLOHEXANE-1,4-DIYL RADICAL CATION BY CEIV-CATALYZED DENITROGENATION OF THE AZOALKANE 1,4-DIPHENYL-2,3-DIAZABICYCLO[2.2.2]OCT-2-ENE AND ITS RELUCTANCE TO UNDERGO COPE REARRANGEMENT [J].

ADAM, W ;

GRABOWSKI, S ;

MIRANDA, MA ;

RUBENACKER, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (02) :142-143

[3] TRIPHENYLPYRYLIUM-SALT-SENSITIZED ELECTRON-TRANSFER OXYGENATION OF ADAMANTYLIDENEADAMANTANE - PRODUCT, FLUORESCENCE QUENCHING, AND LASER FLASH-PHOTOLYSIS STUDIES [J].

AKABA, R ;

SAKURAGI, H ;

TOKUMARU, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (03) :291-297

[4] ELECTRON-TRANSFER PHOTOFRAGMENTATIONS OF 3-PHENYLPROPIOPHENONES [J].

BALDOVI, MV ;

GARCIA, H ;

MIRANDA, MA ;

PRIMO, J .

MONATSHEFTE FUR CHEMIE, 1990, 121 (05) :371-375

[5] HETEROGENEOUS PERMANGANATE OXIDATIONS - AN IMPROVED PROCEDURE FOR THE DIRECT CONVERSION OF OLEFINS TO ALPHA-DIKETONES ALPHA-HYDROXY KETONES [J].

BASKARAN, S ;

DAS, J ;

CHANDRASEKARAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) :5182-5184

[6]

CLIMENT MJ, 1989, HETEROCYCLES, V29, P115

[7] NOVEL PHOTOREACTIONS OF CHROMENE DERIVATIVES - THE PHOTOLYSIS OF 4-ACETOXY-H-2-CHROMENE [J].

CLIMENT, MJ ;

GARCIA, H ;

MIRANDA, MA ;

PRIMO, J .

TETRAHEDRON, 1987, 43 (05) :999-1002

[8] PHOTO FRIES REARRANGEMENTS OF 1-NAPHTHYL ESTERS IN THE SYNTHESIS OF 2-ACYLNAPHTHOQUINONES [J].

CROUSE, DJ ;

HURLBUT, SL ;

WHEELER, DMS .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :374-378

[9] COMPETITIVE REACTIONS OF DIENE CATION RADICALS FORMED ON IRRADIATED METAL-OXIDE SURFACES [J].

FOX, MA ;

SACKETT, DD ;

YOUNATHAN, JN .

TETRAHEDRON, 1987, 43 (07) :1643-1660

[10] THE PHOTOCHEMISTRY OF ALPHA-ACETOXYSTYRENE [J].

GARCIA, H ;

MARTINEZUTRILLA, R ;

MIRANDA, MA .

TETRAHEDRON LETTERS, 1980, 21 (40) :3925-3926