Regio - and stereoselective photocycloadditions of heterocyclic 2,3-diones - Evidence for an unexpected 1,2-aroyl migration

被引：15

作者：

Kollenz, G ^{[1
]}

Terpetschnig, E ^{[1
]}

Sterk, H ^{[1
]}

Peters, K ^{[1
]}

Peters, EM ^{[1
]}

机构：

[1] Graz Tech Univ, Inst Organ Chem, A-8010 Graz, Austria

来源：

TETRAHEDRON | 1999年 / 55卷 / 10期

关键词：

2+2]photocycloadditions; heterocyclic 2,3-diones; 1,2-aroyl migration; X-ray analyses;

D O I：

10.1016/S0040-4020(99)00078-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photocyclization of the heterocyclic 2,3-diones 1a-d with electron rich alkenes affords regio- and stereoselectively the 2+2 adducts 2, from Ib with benzophenone as photosensitizer also the Paterno-Buchi adduct 3 is obtained. Similarly, with phenylethyne the cycloadducts 4 are formed in moderate to low yields, in case of Ic the azepinone 6 is the only reaction product. Thermolysis of 4a generates the pyrono compound 5. Irradiation of the N-arylpyrrolediones le, f and ethylvinyl ether give furo[3,2-c]pyrrolones 7 thus making evident an unexpected 1,2-benzoyl migration. Structural elucidation of all ring systems described is based upon X-ray analyses of 2d, 5 and 7f, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2973 / 2984

页数：12

共 60 条

[1] DETERMINATION OF THE RELATIVE RATES OF FORMATION, FATES, AND STRUCTURES OF TRIPLET 1,4-BIRADICALS GENERATED IN THE PHOTOCHEMICAL CYCLOADDITION REACTIONS OF 2-CYCLOPENTENONES WITH 2-METHYLPROPENE [J].