Regio- and stereoselective photocycloadditions of heterocyclic 2,3-diones — Evidence for an unexpected 1,2-aroyl migration
作者： G. Kollenz , E. Terpetschnig , H. Sterk , K. Peters , E.-M. Peters
DOI: 10.1016/S0040-4020(99)00078-2
关键词: Adduct 、 Reaction product 、 Photosensitizer 、 Chemistry 、 Ring (chemistry) 、 Stereoselectivity 、 Ether 、 Benzophenone 、 Stereochemistry 、 Thermal decomposition
摘要: Abstract Photocyclization of the heterocyclic 2,3-diones 1a-d with electron rich alkenes affords regio- and stereoselectively 2+2 adducts 2, from 1b benzophenone as photosensitizer also Paterno-Buchi adduct 3 is obtained. Similarly, phenylethyne cycloadducts 4 are formed in moderate to low yields, case 1c azepinone 6 only reaction product. Thermolysis 4a generates pyrono compound 5. Irradiation N-arylpyrrolediones 1e, f ethylvinyl ether give furo[3,2-c]pyrrolones 7 thus making evident an unexpected 1,2-benzoyl migration. Structural elucidation all ring systems described based upon X-ray analyses 2d, 5 7f, respectively.
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