2242-68-4Relevant articles and documents
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Maier
, p. 920 (1963)
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The Role of Lithium Amides as Reducing Agents in a Novel Pathway to 3,6-Diarylpyridazines by Ring Transformations of 3,6-Diaryl-s-tetrazines
Hunter, Daniel,Neilson, Douglas G.
, p. 1601 - 1603 (2007/10/02)
3,6-Diaryl-s-tetrazines undergo two competing reactions when treated with lithium amides.The first, direct nucleophilic attack and addition of lithium amide to the tetrazine, appears to be predominant when a less hindered amide is used, and moderate quantities of tetrazine are then regenerated on quenching.The competing reaction, which is seen more clearly with a bulkier amide such as lithium di-isopropylamide, involves reduction of tetrazine to a dihydro derivative with concomitant formation of imine from the amide: this imine is then attacked by further amide and gives rise to a charged intermediate which reacts with more tetrazine to form a pyridazine.