کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1315080 | 1499363 | 2012 | 9 صفحه PDF | دانلود رایگان |
Hydrodefluorination of heptafluoro-2-naphthylamine and its less fluorinated analogues by zinc in aqueous ammonia has been explored with respect to the possibility to occur and to rationalize the product distribution in terms of the mechanism including formation and fragmentation of a polyfluoroarene radical anion.
The combined results of chemical, CVA and quantum-chemical studies provide a mechanistic insight into an interrelation between the regioselectivities of polyfluoro-2-naphthylamines hydrodefluorination and fragmentation of the substrate radical anions.Figure optionsDownload as PowerPoint slideHighlights
► Polyfluoro-2-naphthylamines are reductively hydrodefluorinated by Zn in aq. NH3.
► The reduction energetics has been characterized by CVA measurements.
► The structures of substrate radical anions have been quantum-chemically calculated.
► The radical anions fragmentation regioselectivity correlates with their structures.
► The product distribution is controlled by the radical anions fragmentation.
Journal: Journal of Fluorine Chemistry - Volume 137, May 2012, Pages 64–72