Abstract

The intramolecular addition of benzylic radicals, generated from benzyl phenyl selenides by the action of tris(trimethylsilyl)silane and AIBN or AIBMe, onto neighbouring ketenimine functions is studied. The persistent α-(indol-2-yl)benzyl radicals, resulting from such cyclization processes, undergo cross-coupling with the tert-alkyl radicals arising from the thermal decomposition of the AIBN or AIBMe initiators to give, respectively, 3-(1H-indol-2-yl)propiononitriles 10 or propanoates 14. A rare spiropentacyclic compound 17 containing two indole fragments also resulted from one of these radical reactions. The crystal and molecular structures of 10d and 17 have been solved by X-ray analysis.

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