83470-36-4

Upstream product

• 186581-53-3 diazomethane 
• 193346-78-0 C₂₆H₂₅NO₃P₂ 
• 1084-11-3 bis(4-methylphenyl)phosphinic acid 
• 4129-40-2 di(p-tolyl)phosphinic chloride 
• 193346-72-4 C₂₆H₂₅NO₃P₂ 
• 193346-81-5 C₂₆H₂₅NO₃P₂ 
• 67-56-1 methanol 
• 4129-18-4 di-p-tolylphosphinic azide 
• 73452-53-6 N-(di-p-tolylphosphinoyl)hydroxylamine 

Relevant academic research and scientific papers

Transposition of the phosphinoyl groups in the base-induced rearrangements of N,O-bis(diarylphosphinoyl)hydroxylamines

Because the N- and O-phosphinoyl groups can change places prior to rearrangement, Ph2P(O)NHOP(O)Ar2 and Ar2P(O)NHOP(O)Ph2 (Ar = p-tolyl) both give mixtures of two phosphonamidic-phosphimic anhydrides, Ph(PhNH)P(O)OP(O)Ar2 and Ar(ArNH)P(O)OP(O)Ph2, on treatment with KOBu(t) in Bu(t)OH. The transposition of the phosphinoyl groups may involve phosphorane intermediates (7 and 9) having the P atom contained within a three-membered ring.

DIARYLPHOSPHINIC AZIDES. PHOTOCHEMICAL REACTIONS INCLUDING REARRANGEMENT IN METHANOL

On photolysis in methanol the diarylphosphinic azides Ar2P(O)N3 (Ar=phenyl, p-tolyl, p-anisyl, p-chlorophenyl) rearrange with loss of nitrogen to form (monomeric) metaphosphonimidates which are trapped by the solvent to give methyl NP-diarylphosphonamidates (7) (41-53percent).Diarylphosphinic amides (18-42percent) are also usually formed, presumably from (triplet) nitrenes.The limited evidence available suggests that the rearrangements take place directly from the photo-excited azides rather than via (singlet) nitrene intermediates.One of the products of rearrangement, methyl NP-di(p-chlorophenyl)phosphonamidate, suffers extensive photochemical dechlorination giving methyl N-phenyl-P-p-chlorophenylphosphonamidate.