Issue 44, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
24 Febr. 2023
Accepted
24 Apr. 2023
First published
25 Apr. 2023

Chem. Commun., 2023,59, 6698-6701

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

M. K. Nayak, B. J. Elvers, D. Mandal, A. Das, R. Ramakrishnan, K. R. Mote, C. Schulzke, C. B. Yildiz and A. Jana, Chem. Commun., 2023, 59, 6698 DOI: 10.1039/D3CC00891F

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