Canadian Journal of Chemistry p. 1136 - 1146 (1993)
Update date:2022-08-16
Topics:
Martre, Anne-Marie
Danciu, Virginia
Mousset, Guy
The electrochemical behavior of titanium oxysulfate, used as a redox mediator in the reduction of 4, 4'-dinitrodiben-zyl, is studied in a 5 N H 2S04/EtOH 50: 50 medium. The role played by electrogenerated Ti3+ ions in the chemical reduction of nitro groups is also defined. The results obtained allow the determination of the most suitable conditions leading to selective syntheses. Macroscale electrolyses at a constant potential in the presence of TiOS04 give 4, 4'-diaminodi-benzyl with a great purity and a higher yield (93%) than without mediator (75%). The homogeneous chemical reduction of 4, 4'-dinitrodibenzyl by first electrogenerating the Ti3+ ions, then adding the organic substrate, is particularly selective. The nature of the reduction products depends on the [Ti3+]/[dinitro derivative] ratio. The 4-amino-4'-nitrodiben-zyl is synthesized in a 70% yield for a 6: 1 ratio whereas the amount of diamino derivative increases and can constitute the sole reduction product for higher ratios. A comparison is made with 1, 5-and 1, 8-dinitronaphthalenes and 2, 2'-di-nitrodiphenyl. Using a 6: 1 ratio, l-amino-8-nitronaphthalene is not obtained while 45% of l-amino-5- nitronaphthalene and 25% of 2-amino-2'-nitrodiphenyl are formed by reduction of the corresponding dinitro derivatives.
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(1993)
