74518-46-0Relevant academic research and scientific papers
Phosphoric Carboxylic Imides. Part 6. Structure and Reactivity of 1,3,2-Diazaphospholidine-4,5-diones; Crystal Structure of 1,3-Dimethyl-2-methylamino-1,3,2-diazaphospholidine-2,4,5-trione
Hutton, Alan T.,Modro, Tomasz A.,Niven, Margaret L.,Scaillet, Sonia
, p. 17 - 24 (2007/10/02)
1,3-Dimethyl-2-methylamino-1,3,2-diazaphospholidine-2,4,5-trione (1b) has been synthesized, and its solvolytic behaviour and X-ray crystal structure determined.Methanolysis of (1b) gives products of the cleavage of both imide P-N bonds, indicating that the ring opening in (1b) is much slower than the second P-N cleavage in the ring-opened intermediate.The low reactivity of (1b) is correlated with the small size (92.3 deg) of the endocyclic N-P-N angle, which suggests that not much energy is released upon the formation of the PV trigonal bipyramidal adduct.The molecular structure of (1b) reveals a high degree of coplanarity of the phospholidine ring with both imide N-methyl groups and both carbonyl oxygen atoms.The geometry indicates that the endocyclic nitrogen atoms in (1b) are involved in the resonance interactions not only with the adjacent carbonyl groups, but also with the phosphoryl centre. 1,3-Dimethyl-2-phenoxy-1,3,2-diazaphospholidine-2,4,5-trione (1a) has been found to react with p-anisidine or ammonia exclusively at the phosphorus atom.In the reaction with p-anisidine both P-O bond cleavage (displacement of phenol) and ring P-N bond cleavage products were obtained; this is interpreted in terms of pseudorotation of the initially formed PV intermediate.Ammonia reacts with (1a) giving exclusively the ring-retained, P-OPh bond cleavage products.Our aminolysis results for (1a) contrast with those reported in the literature.
SYNTHESE DE TRIOXO-2,4,5-DIAZA-1,3-PHOSPHOLIDINES-2-TRISUBSTITUTEES ET REACTIONS AVEC LES ALCOOLS ET LES AMINES
Mulliez, M.
, p. 27 - 36 (2007/10/02)
The 2,4,5-trioxo-1,3-diaza-2-phospholidene trisubstituted, 3, are synthetized in the absence of any base, by the reaction of oxalyle chloride on the primary phosphordiamides 1.The 3 cycles are opened with a Formel bond cleavage in the presence of alcohols and a Formel one in the presence of amines.It can be assumed from the results that Formel pentacoordinate X complex is formed, whose breakdown in the case of amines is slower than the attack on one or the other of the carbonyles.
