Rearrangement and fluorination of quinidinone in superacid

In HF/SbF5 at −78 °C, quinidinone 1 yields fluoroketone 3 (50% yield). The reaction implies a cyclic carboxonium ion as an intermediate, which reacts through a concerted rearrangement and fluorination to yield ketone 3.

Graphical abstractIn HF/SbF5 at −78 °C, quinidinone 1 yields fluoroketone 3 (50% yield). The reaction implies a cyclic carboxonium ion as an intermediate, which reacts through a concerted rearrangement and fluorination to yield ketone 3. Figure optionsDownload full-size imageDownload as PowerPoint slide