Bradley Rose - Reduction of an Hexamethylphosphoramide Degradation Product: A Diazabutadiene

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  Publication Details (including relevant citation   information):

  Brad D. Rose, Steven J. Peters, Richard C. Reiter and Cheryl D.   Stevenson, Organic. Letters, 2009, 11 (20), 4564–4567


  Alkali metal over-reduction of an electron acceptor in the   presence of a hydrogen atom donor, in hexamethylphosphoramide   (HMPA), results in a radical that is not simply the anion radical   of the acceptor. This new species exhibits an enigmatic EPR   pattern. Using 15N and 2H labeling studies,   the “HMPA degradation product” was found to be the anion radical   of N,N′-dimethyl-1,4-diazabutadiene. DFT   calculations support this assignment and a mechanism for its   formation.

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