Florence Castan

Use of Phosphorus for Stabilizing Highly Reactive Organic Species: Nitrileimines and Pseudo-Diazoalkenes

Abstract The synthesis and reactivity of several stable nitrile-imines bearing phosphorus groups are described. The use of stable diazomethylenephosphoranes in heterocyclic chemistry is reported.

The surprisingly facile dehydrohalogenation of a hydrazonoyl chloride into a stable phosphorus-substituted nitrilimine

Tetrachloro-o-benzoquinone reacts with bis(diisopropylamino)thioxophosphoranenitrile N-[(phenyl)(2,4,6-trifluoromethylphenyl)phosphanyl]imide 1b affording the corresponding σ5λ5-phosphorus-substituted nitrilimine 2b; addition of HCl to 2b leads to hydrazonoyl chloride 4b which gives back nitrilimine 2b by simple filtration on silica gel.