The Mechanism of Bu₃SnH‐Mediated Homolytic Aromatic Substitution

Abstract

The fate of intermediate π radicals is crucial in Bu3SnH-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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z52419_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.