The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution

Athelstan L.J. Beckwith*, Vincent W. Bowry, W. Russell Bowman, Emma Mann, Jonathan Parr, John M.D. Storey

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    116 Citations (Scopus)

    Abstract

    The fate of intermediate π radicals is crucial in Bu 3SnH-mediated cyclization by homolytic aromatic substitution, for example, of bromo compound 1 via radical 2 to give oxindole 3 (AIBN = azobisisobutyronitrile). The results indicate that the mechanism requires the abstraction of a hydrogen radical from the intermediate π radical by the radical initiator or a product of initiator breakdown, and also that arene solvents are not always the best solvents for radical reactions.

    Original languageEnglish
    Pages (from-to)95-98
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume43
    Issue number1
    DOIs
    Publication statusPublished - 22 Dec 2004

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