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Reduction of an Hexamethylphosphoramide Degradation Product: A Diazabutadiene
Journal article   Peer reviewed

Reduction of an Hexamethylphosphoramide Degradation Product: A Diazabutadiene

Brad D. Rose, Steven J. Peters, Richard C. Reiter and Cheryl D. Stevenson
Organic letters, Vol.11(20), pp.4564-4567
15/10/2009
DOI: https://doi.org/10.1021/ol901798s
PMID: 19769385

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
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 N-15 and H-2 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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