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Synthesis 1990; 1990(8): 649-651
DOI: 10.1055/s-1990-26968
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An Efficient Dechlorination Method for 1,2,3,4-Tetrachloro-5,5-dimethoxycyclopentadiene Diels-Alder Adducts: Inverse Addition-Ethereal Birch Reduction Conditions

David B. Berkowitz*
  • *Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule, CH-8092 Zürich, Switzerland
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Publication Date:
17 September 2002 (online)

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Modified Birch reduction conditions for the selective dechlorination of 1,2,3,4-tetrachloro-5,5-dimethoxycyclopentadiene Diels-Alder adducts are described. Inverse addition of a suspension of lithium in liquid ammonia to a dilute ethereal solution of the adduct at - 78°C gives clean dechlorination with no accompanying alkene reduction.