Reduction of 2-H-substituted pyrrolinium cations: the carbon-carbon single bond in air stable 2,2′-bipyrrolidines as a two-electron-source

Reduction of 2-H-substituted pyrrolinium cations via initially formed secondary radicals results in either dimerisation or H-abstracted products, while the outcome depends on the N-substituents. The resultant central carbon-carbon single bond in the dimerised 2,2 '-bipyrrolidine derivatives can be oxidised chemically and electrochemically. The notably air and moisture-stable dimers were subsequently utilised as a source of two electrons in various chemical transformations.

Automated summary

The reduction of 2-H-substituted pyrrolinium cations results in dimerisation or H-abstracted products, depending on the N-substituents. The dimerised 2,2'-bipyrrolidine derivatives with a central carbon-carbon single bond are stable and can be oxidised chemically or electrochemically. These dimers, which are air and moisture-stable, can serve as a source of two electrons in various chemical transformations.