56956-22-0Relevant academic research and scientific papers
Di-tert-butyl ketone hydrazone and di-tert-butyl ketone triphenyl-phosphoranylidenehydrazone
Villiers, Claude,Thuery, Pierre,Ephritikhine, Michel
, p. o234-o236 (2006)
Reaction of di-tert-butyl ketone with hydrazine hydrate gives di-tert-butyl ketone hydrazone, C9H20N2, which is dimerized by double hydrogen bonding in the solid state. Further reaction of this compound with dibromotriphenylphosphorane gives di-tert-butyl ketone triphenylphosphoranylidene-hydrazone, C27H33N 2P, in the structure of which double chains parallel to the c axis are formed through weak C - H ... n and π-π stacking interactions. The hydrazone group is nearly planar in both cases. In the second compound, one of the aromatic rings is nearly coplanar with the hydrazone moiety, indicating possible π-conjugation.
Di(tert-butyl)diazomethane: Thermal Decomposition and One-Electron Redox Reactions
Bock, Hans,Berkner, Bodo,Hierholzer, Bernhard,Jaculi, Dieter
, p. 1798 - 1815 (2007/10/02)
Di(tert-butyl)diazomethane is a potential precursor for the still unknown, presumably sterically overcrowded tetrakis(tert-butyl)ethane and, therefore, re-investigated.Its (HeI) photoelectron spectrum exhibits a low first vertical ionization energy of only 7.45 eV.Based on the ionization pattern, both the thermal decomposition above 600 K under nearly unimolecular conditions as well as the N2 elimination at the surface of contacts, infinite, infinite, and infinite are analysed in a flow-system.Heterogeneously catalyzed, N2 is split off already at room temperature, but in contrast to results for sterically less shielded diazo compounds, no dimer is formed, and only mixtures of known di(tert-butyl)carbene-isomerization products are isolated.Cyclic voltammetry at 233 K using a glassy carbon electrode proves a reversible oxidation followed by N2 elimination at higher temperatures and an irreversible reduction.On chemical oxidation, however, no paramagnetic species can be detected, whereas chemical reduction at a potassium metal mirror in a THF solution containing (2.2.2)cryptand, yields the radical anion characterized by ESR spectroscopy.Without a cation-chelating ligand, the radical anion of a hitherto unknown dimer, ((CH3)3C)2C=N-N=N-N=C(C(CH3)3)2(1-*), is generated, which dissociates at higher temperature, forming ((CH3)3C)2=N2(1-*).This one-electron reduction product of di(tert-butyl)diazomethane can also be detected after quickly warming up a solution containing presumably the radical anion of the triphenylphosphane adduct ((CH3)3C)2C=N-N-PPh3(1-*).In one of these reduction reactions, a N2 elimination is observed.
