Photochemistry of a benzofuro-annulated oxanorbornadiene formation of propellanes by trapping of an intermediate carbonyl ylide with CN and CC dipolarophiles
作者： Jörg Bussenius , Manfred Keller , Wolfgang Eberbach
DOI: 10.1002/JLAC.1995199508205
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摘要: On photochemical excitation of the benzofuro-annulated oxanorbornadiene 10 in presence dipolarophiles 1:1 addition compounds 11, 22, 23a,b, and 24, respectively, are formed as only monomeric products. The mechanistic interpretation is based on a reaction sequence which involves [2 + 2] photocycloaddition to oxaquadricyclane 12, 1,3-dipolar cycloreversion carbonyl ylide 13 subsequent face-selective trapping by corresponding dipolarophile. No indication transformation highly strained [3]3,6-oxepinophane 14 was obtained. With formation 11 one rare examples cycloaddition nitrile dipolarophile (i.e. acetonitrile) uncovered.
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