Oxidation of Molecules Containing Two Tetraalkylhydrazine Units

Article abstract of DOI:10.1021/jo00361a028

Cyclic voltammetry studies have been carried out on several bishydrazines.Me2NNMe(CH2)nNMeNMe2, n = 2-4 (2-4), and 1,4-bis(dimethylamino)piperazine (11) have only a small separation between their first and second oxidation potentials and give dications which are short-lived in solution (lifetimes below a few milliseconds).In contrast, pentacyclic bishydrazine 14 and tetracyclic bishydrazines 16 and 17 have formal potentials that differ by 0.29, 0.21, and 0.19 V, respectively, and give dications which are long-lived in solution (their lifetimes exceed seconds).Hexacyclic bishydrazines 12 and 13 have a much larger separation in formal pot entials for oxidation and give short-lived dications.The shapes of the tetracyclic and pentacyclic compounds are discussed, as is the implication of these results for the consideration of a hydrazine radical cation interacting with a neutral hydrazine.