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Radical cation Diels-Alder reaction of indoles and exocyclic dienes

✍ Scribed by Olaf Wiest; Eberhard Steckhan

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
223 KB
Volume
34
Category
Article
ISSN
0040-4039

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The photoinduced electron transfer catalyzed radical cation Diels-Alder reaction between exocyclic dienes containing an N-O or N-N bond as an intentional cleaving point in the ring moiety [cf. (IV) and (X)] and indoles provides a rapid access to highly functionalized tetrahydrocarbazole derivatives

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Photoinduced electron transfer (PET) initiates radical-cation Diels Β± Alder reactions between indole and exocyclic dienes. As catalysts, triarylpyrylium tetrafluoroborates are used. The products are [b]-anellated tetrahydrocarbazoles, which are not accessible through neutral cycloadditions. The resu