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Synthesis 1986; 1986(4): 326-328
DOI: 10.1055/s-1986-31602
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An Improved Synthesis of 2,3-Norbornadienoanthracene and its Application to the Synthesis of Anthracene Annellated Norbornenylogs

Harish K. Patney* , Michael N. Paddon-Row
  • *Department of Chemistry, New South Wales Institute of Technology, P.O. Box 123, Broadway, New South Wales 2007, Australia
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Publication History

Publication Date:
27 September 2002 (online)

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An improved synthesis of the title compound 1 is reported and involves the thermal cycloaddition of 1,4-naphthoquinone 3 to cyclopentadiene and subsequent treatment of the resulting adduct 4 with lithium aluminium hydride followed by tosyl chloride in pyridine. That 1 can provide access to a variety of anthracene annellated norbornyl compounds is exemplified by the synthesis of 9 through ruthenium-catalysed thermal cycloaddition of dimethyl acetylenedicarboxylate to 1, followed by cycloaddition of quadricylane to the resulting adduct 8.

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