Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N'-Dioctyl-4,4'-bipyridinium Radical Cation in Two-Phase Systems

Article abstract of DOI:10.1021/ja00333a017

Photochemical and chemical reduction of N,N'-dioctyl-4,4'-bipyridinium (C8V(2+), 1) to the corresponding radical cation C8V(1+.) (2) leads to an induced disproportionation of C8V(1+)^. in a water-organic two-phase system.This process yields the two-electron reduction product N,N'-dioctyl-4,4'(1H,1H')-bipyridylidene (C8V, 3).The induced disproportionation reaction is a result of opposite solubility properties of the disproportionation products in the two phases.The two-electron reduction product C8V (3) mediates the debromination of 1,2- and 1,1-dibromo substrates.