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.
|Number of pages||8|
|Journal||Journal of the American Chemical Society|
|Publication status||Published - 1992 Jul 1|
ASJC Scopus subject areas
- Colloid and Surface Chemistry