RADICAL IONS AND PHOTOCHEMICAL CHARGE-TRANSFER PHENOMENA .32. CYCLOBUTANE AND CYCLOPROPANE RING-OPENING REACTIONS BY PHOTOINDUCED ELECTRON-TRANSFER - A NEW RING EXPANSION METHOD

被引：19

作者：

BISCHOF, EW ^{[1
]}

MATTAY, J ^{[1
]}

机构：

[1] UNIV MUNSTER,INST ORGAN CHEM,ORLEANS RING 23,W-4400 MUNSTER,GERMANY

来源：

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 1992年 / 63卷 / 02期

关键词：

D O I：

10.1016/1010-6030(92)85143-I

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new reductive ring cleavage reaction, induced by photoinduced electron transfer (PET), is applied to three- and four-membered ring systems containing a carbonyl function in the a position to the strained ring. Introducing substituents which stabilize radical intermediates changes the outcome of the reaction to yield linearly fused ring systems that may be of interest in natural product synthesis.

引用

页码：249 / 251

页数：3

共 11 条

[1] RADICAL IONS AND PHOTOCHEMICAL CHARGE-TRANSFER PHENOMENA .29. RADICAL ANIONIC CYCLIZATION REACTIONS VIA PHOTOCHEMICALLY INDUCED ELECTRON-TRANSFER [J].

BISCHOF, EW ;

MATTAY, J .

TETRAHEDRON LETTERS, 1990, 31 (49) :7137-7140

[2]

BISCHOF EW, 1990, 13TH IUPAC S PHOT

[3] RADICAL-ANION RING-OPENING REACTIONS VIA PHOTOCHEMICALLY INDUCED ELECTRON-TRANSFER [J].

COSSY, J ;

ACLINOU, P ;

BELLOSTA, V ;

FURET, N ;

BARANNELAFONT, J ;

SPARFEL, D ;

SOUCHAUD, C .

TETRAHEDRON LETTERS, 1991, 32 (10) :1315-1316

[4] SYNTHETIC APPLICATIONS OF INTRAMOLECULAR ENONE OLEFIN PHOTOCYCLOADDITIONS [J].

CRIMMINS, MT .

CHEMICAL REVIEWS, 1988, 88 (08) :1453-1473

[5]

DEMUTH M, 1989, SYNTHESIS-STUTTGART, P145

[6] MECHANISMS OF PHOTOCHEMICAL REACTIONS IN SOLUTION .44. PHOTODIMERIZATION OF CYCLOHEXENONE [J].

LAM, EYY ;

VALENTIN.D ;

HAMMOND, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (14) :3482-&

[7] RING EXPANSIONS OF [2 + 2] PHOTOADDUCTS - POTENTIAL APPLICATIONS IN THE SYNTHESIS OF TRIQUINANE AND TAXANE SKELETONS [J].

LANGE, GL ;

DECICCO, CP ;

WILLSON, J ;

STRICKLAND, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1805-1810

[8] [3+2] CYCLOADDITIONS WITH AZIRINE RADICAL CATIONS - A NEW SYNTHESIS OF N-SUBSTITUTED IMIDAZOLES [J].

MULLER, F ;

MATTAY, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (10) :1336-1337

[9] PHOTOREACTIVITY OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - COMPETITIVE 2-CYCLOHEXENONE DIMERIZATION AND ADDUCT FORMATION WITH TRIETHYLAMINE [J].

PIENTA, NJ ;

MCKIMMEY, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (20) :5501-5502

[10]

Schuster D. I., 1989, CHEM ENONES 2, P623

← 1 2 →