Photoinduzierte Elektronenübertragungsreaktionen zwischen aromatischen Diazoniumkationen und Anionen
1985; Wiley; Volume: 327; Issue: 3 Linguagem: Inglês
10.1002/prac.19853270306
ISSN0021-8383
AutoresH. G. O. Becker, G. Israel, U. Oertel, Hans‐Ulrich Vetter,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoPhotoinduced Electron Transfer between Arenediazonium Cations and Anions Anions X ⊖ can act as donors in electron transfer reactions to photoexcited arenediazonium ions. The yield of the arene formed in this reaction increases with decreasing electrochemical oxidation potential E of X ⊖ (X ⊖ = BPh 4 ⊖ , Br ⊖ , HOOCCOO ⊖ , Cl ⊖ , BF 4 ⊖ ). The oxidized donor X· (Cl·, ·COO ⊖ ) and aryl radicals Ar· benig intermediates of the reductive dediazoniation of ArN 2 ⊖ can be detected by spin trapping with nitrosodurene (ND) and phenyl‐tert‐butylnitrone (PBN). A solvent effect in the electron transfer reaction is interpreted in terms of ion pairing, where the electron transfer is favored by preorientation and a short distance between the electron donor and the acceptor previous to excitation of ArN 2 ⊖ by light.
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