Diaminophosphonium diazaylides 2 react under mild conditions with diphenylacetyl chloride, to afford diphenyl-N-(substituted)ketenimines 4 or, depending on the case, their transformation products: either the tautomer 8, or the dimer 9. The general reaction seems to proceed firstly via an elimination step on the acid chloride followed then by an aza-Wittig reaction between the resulting ketene 7 and
The first examples of metalated stabilized diaminophosphonium diazaylides 7 have been synthesized in good yields from acylazides by two different synthetic pathways involving either an original and direct Staudinger reaction with the sodium phosphide (diazaylides 7′) or a more classical Staudinger reaction with diphenylphosphine and a subsequent deprotonation (diazaylides 7′). Additionally, the related new diaminophosphonium monoazaylides 6 and diaminophosphonium salts 5 have also been synthesized.