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Synlett 1997; 1997(SI): 469-470
DOI: 10.1055/s-1997-6134
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Synthesis of Alkylidenecyclopropanes via Thermal Cycloreversion of α-Spirocyclopropyl-β-Lactones

Rick L. Danheiser* , Thomas W. Lee, Maria Menichincheri, Steven Brunelli, Masaki Nishiuchi
  • *Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139
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Publication Date:
31 December 2000 (online)

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An efficient two-step synthesis of alkylidenecyclopropanes is reported based on the addition of metallated cyclopropyl thiol esters to carbonyl compounds. Thermolysis of the resulting α-spirocyclopropyl-β-lactones at 105-150 °C induces thermal [2+2] cycloreversion to furnish alkylidenecyclopropanes in goody yield.

alkylidenecyclopropanes - β-lactones - [2+2] cycloreversion - thiol esters