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Synlett 1995; 1995(12): 1241-1242
DOI: 10.1055/s-1995-5232
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Facile One-Pot Preparation of Functionalized Bicyclo[4.2.1]nonan-9-one Precursors of Carbocyclic Eight-Membered Rings

Tania Lavoisier, Jean Rodriguez*
  • *Laboratoire RéSo, Réactivité en Synthèse Organique, URA au CNRS 1411, Centre de St-Jérôme, boîte D12, 13397 Marseille cedex 20, France
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Publication Date:
31 December 2000 (online)

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Diactivated cyclopentanones undergo a base promoted one-pot tandem α,α’-dialkylation process with 1,4-dihalides leading to functionalized bicyclo[4.2.1]nonan-9-one derivatives, which are easily transformed to eight-membered rings through a high yield reverse-Dieckmann cleavage.

Cycloalkylation - bicyclo[4.2.1]nonanes - retro-Dieckmann - eight-membered rings