Tethered CAAC-CAAC dimers: oxidation to persistent radical cations and bridging-unit dependent reactivity/stability of the dications

Herein, we report tethered cyclic(alkyl)(amino)carbene (CAAC) dimers in which two CAAC-motifs are connected by an ethylene-, trans-1,2-cyclohexylene- and propylene-spacer through their N-centres. The 1-electron oxidized radical cations are isolable, whereas a significant influence of the bridging unit on the chemical reactivity becomes apparent in and with the 2-electron oxidized products.

Automated summary

In this study, tethered cyclic(alkyl)(amino)carbene (CAAC) dimers were reported, in which two CAAC motifs are connected by an ethylene-, trans-1,2-cyclohexylene- and propylene-spacer through their N-centres. The 1-electron oxidized radical cations are isolable, and the bridging unit significantly affects the chemical reactivity in and with the 2-electron oxidized products.