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Synlett 1992; 1992(6): 476-479
DOI: 10.1055/s-1992-21382
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Starburst Spiroannulation and X-Ray Crystal Structure of 6-Cyclopropylidene-5-oxaspiro[2.3]-hexan-4-one

Andreas Wulferding* , Rudolf Wartchow, H. Martin R. Hoffmann
  • *Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-3000 Hannover, Germany
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Publication Date:
08 March 2002 (online)

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The title lactone 1 has been prepared from 1-bromo-cyclopropanecarbonyl chloride on a gram scale by an organo-metallic route combined with ultrasonication. Its X-ray crystal structure reveals a planar cyclopropylidenemethoxy fragment with a very short exocyclic carbon-carbon double bond [1.287(4)Å]. The reaction with enamines furnishes functionalized tetracyclic cyclohexane-1,3-diones. Even medium and large rings combine to give isolable Mannich bases.

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