The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution
Athelstan L. J. Beckwith Prof.
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia, Fax: (+61) 2-6253-0737
Search for more papers by this authorVincent W. Bowry Dr.
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia, Fax: (+61) 2-6253-0737
Search for more papers by this authorW. Russell Bowman Prof.
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK, Fax: (+44) 1509-223-925
Search for more papers by this authorEmma Mann Dr.
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK, Fax: (+44) 1509-223-925
Search for more papers by this authorJonathan Parr Dr.
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK, Fax: (+44) 1509-223-925
Search for more papers by this authorJohn M. D. Storey Dr.
Department of Chemistry, Meston Building, University of Aberdeen, Old Aberdeen AB24 3UE, UK, Fax: (+44) 1224-272-921
Search for more papers by this authorAthelstan L. J. Beckwith Prof.
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia, Fax: (+61) 2-6253-0737
Search for more papers by this authorVincent W. Bowry Dr.
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia, Fax: (+61) 2-6253-0737
Search for more papers by this authorW. Russell Bowman Prof.
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK, Fax: (+44) 1509-223-925
Search for more papers by this authorEmma Mann Dr.
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK, Fax: (+44) 1509-223-925
Search for more papers by this authorJonathan Parr Dr.
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK, Fax: (+44) 1509-223-925
Search for more papers by this authorJohn M. D. Storey Dr.
Department of Chemistry, Meston Building, University of Aberdeen, Old Aberdeen AB24 3UE, UK, Fax: (+44) 1224-272-921
Search for more papers by this authorGraphical 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
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