Carbanions: Electron Transfer vs. Proton Capture. 8. Use of Sterically Protected Aromatic Nitro Compounds as Base-Resistant, One-Electron Oxidants

Article abstract of DOI:10.1021/jo00381a005

The behavior of two sterically protected nitroarenes, 2,4,6-tri-tert-butylnitrobenzene and 1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-nitroanthracene, was studied in the presence of strong bases.These compounds are resistant to the oxygen-base-promoted reactions observed with nitrobenzene, but they retain the capacity to oxidize carbon bases such as 9-methoxyfluorenide and triphenylmethide ions.Alkyllithium compounds are converted to alkyl radicals but phenyllithium does not react.Unexpectedly, the radical anions formed when these nitro compounds serve as oxidants undergo slow denitration to the corresponding aryl radicals.