Phosphazo compounds

Conversion o( organic azides with phosphines or phosphites to Immophosphoranes (phosphazo compounds) and their hydrolysis to amines. 

Phosphazo compounds (e.g. iminophosphoranes) from the reaction of tertiary phosphine (Example PhsP) with organic azides. 

A. V. Kirsanov, Phosphazo-Compounds, Naukova Dumka, Kiew 1965. 

This reaction represents the best general method for amide preparation. Cold, concentrated aqueous ammonia is used as in the preparation of iso-butyramide (83%),or the reaction may be carried out by passing dry ammonia into a solution of the acyl halide in anhydrous ether as in the formation of cyclopropanecarboxamide (91%). Separation of the amide from ammonium chloride is usually accomplished by extraction of the amide by organic solvents. Aqueous sodium hydroxide is employed to take up the hydrogen chloride when amine hydrochlorides are used in place of the free amines as in the preparation of N-methylisobutyramide (75%). When phosphorus trichloride is added to a mixture of an amine and a carboxylic acid, phosphazo compounds, RN=PNHR, rather than acyl halides, are believed to be intermediates. These compounds have been shown to react with carboxylic acids to give amides. ... 

Conversion ot organic azides with ptiosphines or ptwspMes to hnmopnosptwranes (phosphazo compounds) and their hydroiysis to amines. 

Staudinger reaction. Synthesis of phosphazo compounds by the reaction of tertiary phosphines with organic azides. 

V-Aminoazoles react with the PhjP-Brj complex in the presence of mild bases to give phosphazo compounds 295, which are transformed to a-chlorohydrazones 296 under the action of acylchlorides (88HI935). 

Triazolo[3,4-Z>]thiadiazolium salts (450) are prepared by three methods (1) acidic cyclization of N-acylaminothiones 449, (2) the action of PCI5 on Schiff bases 451, and (3) interaction of phosphazo compounds 452 with acyl halogenides. On the basis of phosphazo compounds and acyl isothiocyanates, betaines 453 have also been synthesized (86LA1540). 

Amidines. 2. Guanidines. 3. Phosphazo compounds. 4. Organic bases. I. 

CeH,),P [(CH,),NkP l(CH,m,PO Phosphinic acid amides Phenyl phosphorodi-(1-imidazolidate) Phosphazo compounds Trichlorophosphazo-sulfonyl compounds Phenylphosphonic dichloride (C,H,),PO... 

Phosphazo compounds (monophosphazenes) were first produced from tertiary phosphines and organic azides in 1919 by the Staudinger reaction [6,7], This reaction proceeds via an unstable phosphazide intermediate. 

Dimethylphosphono-diazomethane Phenyl phosphorodi-(1-imidazolidate) Phosphazo compounds T richlorophosphazo-sulfonyl compounds Phenylphosphonic dichloride... 

Dimethylphosphono-diazomethane Phenyl phosphorodi-(Idmidazolidate) Phosphazo compounds Trichlorophosphazo-sulfonyl compounds N,PmCH,),],PFf (C,Hfi),PON, (C,H,),PO 1 -Ethy l-3-methy 1-3-phospholine 1-oxide P2O,... 

Phosphazo compounds Trichlorophosphazo-sulfonyl compounds Phenylphosphonic dichloride P2O,... 

Phosphazo compounds s. Phosphine imines Phosphine dihalides... 

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