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Synlett 1990; 1990(5): 275-277
DOI: 10.1055/s-1990-21063
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Photoinduced, Electron-Transfer-Catalyzed Diels-Alder Reaction Between Indole and 1,3-Cyclohexadienes1

Andreas Gieseler* , Eberhard Steckhan, Olaf Wiest
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-5300 Bonn 1, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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Triarylpyrylium tetrafluoroborates are very effective sensitizers for the photoinduced (450 W Xenon arc lamp or 250 W slide projector with halogen lamp), electron-transfer-catalyzed Diels-Alder reaction between indole and substituted 1,3-cyclohexadienes, if acyl chlorides are used as trapping agents. Thus 9-acyl- 4,4a,9,9a-tetrahydro-1,4-ethano-1H-carbazoles are generated in one step (6 examples) with practically total regioselectivity, such that a substituent in the 1-position of the 1,3-cyclohexadiene is always found in the 1-position of the tetrahydrocarbazole.