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Synthesis 1991; 1991(7): 565-566
DOI: 10.1055/s-1991-26516
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Synthesis and Flash Vacuum Pyrolysis of Dimethyl anti-7-Nitro-2,5-norbornadiene-2,3-dicarboxylate

Alan P. Marchand* , S. Pulla Reddy, Paritosh R. Dave
  • *Department of Chemistry, University of North Texas, Denton, TX 76203-5068, USA
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Publication Date:
29 April 2002 (online)

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Reaction of dimethyl anti-7-(trimethylsilyl)-2,5-norbornadiene-2,3-dicarboxylate (dimethyl anti-7-(trimethylsilyl)bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate, 1) with nitronium tetrafluoroborate affords the title compound 2 (65%). Subsequent photolysis of 2 affords the corresponding substituted quadricyclane derivative 3 (75%). Flash vacuum pyrolysis of 2 at 600°C affords dimethyl phthalate (67%) as the only isolable product.