Base-Induced Addition-Elimination Reactions of Electron-Deficient Vinylarenes Containing a Carbonyl or Ester Group Utilizing 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD)

Article abstract of DOI:10.1246/bcsj.64.3188

The reaction of electron-deficient vinylarenes such as styrylketones and cinnamate with PTAD afforded double Diels-Alder products and Diels-Alder ene products; the latter underwent novel base-induced elimination of 4-phenyl-1,2,4-triazoline-3,5-dione via a stable carbanion.