ELECTRON-TRANSFER PROCESSES .20. CONVERSION TO PARA,PARA'-DINITROSTILBENE AND OTHER EXAMPLES OF THE SRN1 SUBSTITUTION-REACTIONS OF PARA-NITROBENZYL DERIVATIVES

The following reactions have been demonstrated to proceed by electron-transfer mechanisms and to involve intermediate radicals and radical anions: (a) the coupling of the anion of 2-nitropropane with N-(p-nitrobenzyl)pyridinium chloride to form 2-nitro-2-methyl-l-(p-nitrophenyl)propane; (b) the coupling of the anion of 2-nitropropane with p-nitro-α, α-dimethylbenzyl phenyl sulfoxide or sulfone to yield 2-nitro-3-(p-nitrophenyl)-2, 3-dimethylbutane; (c) the base-catalyzed coupling of p-nitrobenzyl chloride or dimethyl-p-nitrobenzylsulfonium bromide to give, p, p'-dinitrostilbene; (d) the substitution reaction of thiophenoxide ion with p-nitro-α.α-dimethylbenzyl phenyl sulfoxide or sulfone to yield p-nitro-α, α-dimethylbenzyl phenyl sulfide. © 1979, American Chemical Society. All rights reserved.