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Synlett 1997; 1997(1): 69-70
DOI: 10.1055/s-1997-708
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Vinylcyclopropylacyl Radicals: Intramolecular Ketene Additions leading to Concise Syntheses of Cyclohexenones

Nicola Herbert, Gerald Pattenden*
  • *Department of Chemistry, Nottingham University, Nottingham NG7 2RD, England
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Publication Date:
22 March 2004 (online)

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Treatment of a range of vinylcyclopropyl selenyl esters with Bu3SnH-AIBN produces cyclohexenone products (50-60%) via 6-exo-dig radical cyclisations involving ketene intermediates.

α,β-unsaturated acyl radical - addition to ketenes - cyclohexenone