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Issue 5, 2004
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Persistent radical effect in the intramolecular addition of benzylic radicals onto ketenimines: selective cross-coupling of α-(indol-2-yl)benzyl radicals with the 1-cyano-1-methylethyl radical

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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.

Graphical abstract: Persistent radical effect in the intramolecular addition of benzylic radicals onto ketenimines: selective cross-coupling of α-(indol-2-yl)benzyl radicals with the 1-cyano-1-methylethyl radical

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Publication details

The article was received on 15 Oct 2003, accepted on 11 Feb 2004 and first published on 23 Mar 2004


Article type: Paper
DOI: 10.1039/B312930F
Citation: New J. Chem., 2004,28, 570-577
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    Persistent radical effect in the intramolecular addition of benzylic radicals onto ketenimines: selective cross-coupling of α-(indol-2-yl)benzyl radicals with the 1-cyano-1-methylethyl radical

    M. Alajarín, A. Vidal, M. Ortín and D. Bautista, New J. Chem., 2004, 28, 570
    DOI: 10.1039/B312930F

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