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Generation and Reactions of Radical Cations From the Photolysis of Aromatic Compounds With Tetranitromethane in 1,1,1,3,3,3-Hexa-Fluoropropan-2-OL

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image of Research on Chemical Intermediates

The generation and reactions of aromatic radical cations by photolysis of ArH-tetranitromethane in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP) at room temperature has been investigated. The primary radical cations (ArH.+) were detectable by EPR spectroscopy in most cases where E°(Ar.+/ArH) 1.5 V (vs. Ag/AgCl). Secondary radical cations were obtained from pentamethylbenzene and durene (1,2,3,4,5,6,7,8-octamethyl- and 1,2,4,5,6,8-hexamethyl-anthracene radical cation), from certain naphthalenes (dehydrodimer radical cations, Ar-Ar.+) and from 2,3-dimethylanisole (the radical cation of a nitroso derivative). The persistence of the radical cations in the presence of trinitromethanide ion is seen as a consequence of the stabilization of the nucleophile by HFP. This assumption was supported by preparative results on 1-methoxynaphthalene and 1,4-dimethylnaphthalene, where the trinitromethanide ion initiated pathway was completely eliminated in HFP, contrary to results earlier obtained in dichloromethane.

Affiliations: 1: Chemical Center, Lund University, P.O. Box 124, S-221 01 Lund, Sweden; 2: Department of Chemistry, University of Canterbury, Christchurch, New Zealand


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