Di-tert-butyl ketone hydrazone and di-tert-butyl ketone triphenylphosphoranylidenehydrazone

Abstract

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 triphenyl­phosphoranyl­idene­hydrazone, C27H33N2P, in the structure of which double chains parallel to the c axis are formed through weak C—H⋯π 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.