A Hyper-Reactive Tetrafluorinated Cumulene

Significance

The authors report on the utility of the hyper-reactive tetrafluorobutatriene in the Diels-Alder reaction. Traditionally, this reagent has been very difficult to prepare and too unstable to use in reactions. Utilizing a recent, more efficient synthesis of the triene (A. Bach et al. Angew. Chem. Int. Ed. 2002, 41, 296), the authors were able to prepare the reagent and subsequently test the triene with a variety of dienes. In many reactions, conversion into the product is instantaneous and quantitative. The Diels-Alder products are stable to standard chromatographic work-up.