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Synthesis 1986; 1986(4): 328-330
DOI: 10.1055/s-1986-31603
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An Efficient Synthetic Strategy for Naphthalene Annellation of Norbornenylogous Systems

Michael N. Paddon-Row* , Harish K. Patney
  • *Department of Chemistry, University of New South Wales, P. O. Box 1, Kensington, New South Wales 2033, Australia
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Publication Date:
27 September 2002 (online)

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Naphthalene annellation of norbornyl compounds can be readily achieved in good yields through in situ trapping of dibromonaphthoquinone (5), generated from 4 and sodium iodide, by the dienophilic norbornyl substrate. The dienophiles used include norbornadiene (which gave mono-adduct 8b or bis-adduct 3a depending on the conditions), norbornene, benzonorbornadiene (11), diene 9, and 13.