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Synthesis 1985; 1985(10): 949-950
DOI: 10.1055/s-1985-31397
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Metal-Assisted Entry into the Bicyclo[4.2.1]nona-2,4-diene System

Zeev Goldschmidt* , Elisheva Genizi
  • *Department of Chemistry, Bar-Ilan University, Ramat-Gan 52100, Israel
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Publikationsdatum:
27. September 2002 (online)

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The present first synthesis of 7,7,8,8-tetracyanobicyclo[4.2.1] nona-2,4-diene involves a novel thermal rearrangement of the readily available [3 + 2] cycloadduct of cycloheptatriene-Fe(CO)3 with tetracyanoethylene to 7,7,8,8-tetracyanobicyclo[4.2.1]nona-2,4-diene-Fe(CO)3, followed by oxidative disengagement of the metal fragment with ceric ammonium nitrate. The rearrangement is best effected in polar solvents.