Thermal Reactions of Substituted Cyclopropenone Acetals. Regio-and Stereochemistry of Vinylcarbene Formation and Low-Temperature [3 + 2] Cycloaddition

Hidetoshi Tokuyama, Masahiko Isaka, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

Cyclopropenone acetals bearing olefinic substituents of diverse electronic character have been synthesized and examined for their thermal behavior toward water and electron-deficient olefins. The substituted cyclopropenes underwent regio-and stereoselective hydration to give acrylate derivatives via vinylcarbene species, providing new data on the regio-and stereochemistry of vinylcarbene species. They also underwent regioselective [3 + 2] cycloadditions to electron-deficient olefins to give a variety of cyclopentenone acetals. In particular, phenylthio and ester substituents connected to the cyclopropene carbon effected highly regioselective vinylcarbene formation below room temperature to permit the thermal [3 + 2] cycloaddition to take place under extremely mild conditions.

Original languageEnglish
Pages (from-to)5523-5530
Number of pages8
JournalJournal of the American Chemical Society
Volume114
Issue number14
DOIs
Publication statusPublished - 1992 Jul 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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