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

Ruben Maidan, Zafrir Goren, Itamar Willner, Janies Y. Becker

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80 Scopus citations

Abstract

Photochemical and chemical reduction of N,N′-dioctyl-4,4′-bipyridinium (C8V2+, 1) to the corresponding radical cation C8V+· (2) leads to an induced disproportionation of C8V+· 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.

Original languageEnglish
Pages (from-to)6217-6222
Number of pages6
JournalJournal of the American Chemical Society
Volume106
Issue number21
DOIs
StatePublished - 1984

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