Limits to oxidation of organic substrates. SET oxidative processes of commonly used solvents as revealed through the photochemical reaction with 1,2,4,5-benzenetetracarbonitrile

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Abstract

The chemical reactivity upon single electron transfer of some common solvents has been explored. This has been obtained by using photo excited benzene-1,2,4,5-tetracarbonitrile (TCB) as the oxidant. Under this condition acetonitrile, isobutyronitrile, methanol and trifluoroethanol all undergo α-deprotonation from their radical cations giving alkyl radicals which are trapped by TCB-· and yield alkylbenzenetricarbonitriles or products derived from them. The reaction of the two aliphatic nitriles occurs only in the presence of protic additives, and is accompanied by a different fragmentation leading to methyl (or respectively isopropyl) radicals. Trifluoroacetic acid decarboxylates, probably via oxidation of the anion. TCB irradiation in neat methanol (rather than in MeOH-MeCN mixtures) leads to protic addition onto the cyano group, finally giving dicyanoindoles.

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Fagnoni, M., Vanossi, M., Mella, M., & Albini, A. (1996). Limits to oxidation of organic substrates. SET oxidative processes of commonly used solvents as revealed through the photochemical reaction with 1,2,4,5-benzenetetracarbonitrile. Tetrahedron, 52(5), 1785–1796. https://doi.org/10.1016/0040-4020(95)01013-0

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