Phosphonic acid anhydrides

PPA (propane phosphonic acid anhydride) has a low tendency to racemization. By-products that are formed are water-soluble and thus easily removed. ... 

Scheme 10. Reagents and conditions (a) KHMDS, THF (b) LiOH, THF/H2O (c) CICO2/BU, EtsN, NaNs 20-65 °C (d) quinolone-4-carboxylic acid, propane phosphonic acid anhydride, EtsN.

Propane phosphonic acid Anhydride 35 Mixed anhydride Water-soluble by-products ease work-up. 

Propane phosphonic acid anhydride coupling, mineral/resin composite strength, elastomers... 

A similar PPE (Scheme 6.21) containing phosphonate groups has been reported by the coupling of 1,4-diethynylbenzene to 46 [82]. The polymer 48 is soluble in organic solvents. Deprotection by boron tribromide in lutidine and hydrolysis of the mixed boronic and phosphonic acid anhydride in sodium... 

Phosphorus(III) Oxide. Phosphoms(III) oxide [12440-00-5] the anhydride of phosphonic acid, is formed along with by-products such as phosphoms pentoxide and red phosphoms when phosphoms is burned with less than stoichiometric amounts of oxygen (62). Phosphoms(III) oxide is a poisonous, white, wax-like, crystalline material, which has a melting point of 23.8°C and a boiling point of 175.3°C. When added to hot water, phosphoms(III) oxide reacts violentiy and forms phosphine, phosphoric acid, and red phosphoms. Even in cold water, disproportionation maybe observed if the oxide is not well agitated, resulting in the formation of phosphoric acid and yellow or orange poorly defined polymeric lower oxides of phosphoms (LOOP). 

A dispersant that can be used in drilling fluids, spacer fluids, cement slurries, completion fluids, and mixtures of drilling fluids and cement slurries controls the rheologic properties of and enhances the filtrate control in these fluids. The dispersant consists of polymers derived from monomeric residues, including low-molecular-weight olefins that may be sulfonated or phosphonated, unsaturated dicarboxylic acids, ethylenically unsaturated anhydrides, unsaturated aliphatic monocarboxylic acids, vinyl alcohols and diols, and sulfonated or phosphonated styrene. The sulfonic acid, phosphonic acid, and carboxylic acid groups on the polymers may be present in neutralized form as alkali metal or ammonium salts [192,193]. 

Polymer Media Polymaleic Anhydride Poly Acrylic Acid Polyvinyl Phosphonic Acid Polyvinyl Sulfonic Acid Polystyrene Sulfonate Tripoly Phosphate... 

Mitsubishi have reported several processes based on Ru-catalyzed hydrogenation of anhydrides and acids. Succinic anhydride can be converted into mixtures of 1,4-butane-diol and y-butyrolactone using [Ru(acac)3]/trioctylphosphine and an activator (often a phosphonic acid) [97]. Relatively high temperatures are required ( 200°C) for this reaction. The lactone can be prepared selectively under the appropriate reaction conditions, and a process has been developed for isolating the products and recycling the ruthenium catalyst [98-100]. 

Metal ions have been shown to catalyze the hydrolysis of phosphate esters, phosphoric and phosphonic acid halides, and various phosphoric acid anhydrides including acyl phosphates, pyrophosphate derivatives, and ATP. 

Synthesis and Properties of Anhydrides of Phosphonous and Phosphonic Acids and Their Thioanalogs... 

Radical-based dephosphorylation via a phosphonyl radical constitutes one formulation for the mechanism of C-P bond cleavage during microbial degradation of organophospho-nates.80 Frost has demonstrated that anhydrides 117 derived from phosphonic acid and thiohydroxamic acid react in a chain sequence with thiols, Bu3SnH and CC14 to give dephosphoryl-... 

Various acids (nitrobenzoic acids, picric acid, toluenesulfonic and phosphonic acids) have been reacted with isonitriles to give mixed anhydrides (246 equation 135). ... 

Metaphosphonic Acid Anhydrides. In a related process, the fragmentation of compounds 5 (77) and 7 (7) by thermal or photochemical means releases fragments (6 or 8) that are the metaanhydrides of phosphonic acids. The properties of these species are very similar to those of the metaphosphates. 

We noted that a small amount of anhydride 41 was formed in the photolysis of 32 when no added hydroxylic reactant was present. Presumably a trace of water is responsible for the small amount of fragmentation that occurred. The anhydride may arise from the photo-addition of the initially formed phosphonic acid 40 to the phosphoryl group, followed by fragmentation. 

Hampton, A., Sasaki, T., and Paul, B., Synthesis of 6 -cyano-6 -deoxyhomoadenosine-6 -phosphonic acid and its phosphoryl and pyrophosphoryl anhydrides and studies of their interactions with adenine nucleotide utilizing enzymes, J. Am. Chem. Soc., 95, 4404, 1973. 

Coppola, G.M., Hardtmann, G.E., and Pfister, O.R., Chemistry of 2//-3,l-bcn/.oxazinc-2,4(l//)-dione (isatoic anhydride). Part 2. Reactions with thiopseudoureas and carbanions, J. Org. Chem., 41, 825,1976. Kabachnik, M.L, Rossiiskaya, P.A., and Shepeleva, E.S., Esters of a-keto phosphonic acids. Part 3. Two types of carboxylic acid derivatives, Izv. Akad. Nauk SSSR, Ser. Khim., 163, 1947 Chem. Abstr, 42, 4132i, 1948. 

Zhang, J., and Xu, X., Total synthesis of 6-ep/-sarsolilide A, Tetrahedron Lett., 41, 941, 2000. Boehm, H.M.. I landa, S., Pattenden, G., Roberts. L.. Blake, A.J., and Li, W.-S., Cascade radical cyclizations leading lo steroid ring constructions. Regio- and stereo-chemical studies using ester- and fluoroalkene substituted polyene acyl radical intermediates.,/. Chem. Soc., Perkin Trans. 1, 3522, 2000. Hampton, A.. Sasaki, T, and Paul, B., Synthesis of 6 -cyano-6 -deoxyhomoadenosine-6 -phosphonic acid and its phosphoryl and pyrophosphoryl anhydrides and studies of their interactions with adenine nucleotide utilizing enzymes, J. Am. Chem. Soc.. 95. 4404, 1973. 

Nylen (1930) converted the sodium salt of diethyl phosphonate with diethyl phosphorochloridate (8) and oxidised the mixed phosphorus acid-phosphoric acid anhydride obtained ... 

PHOSPHONIC ACID (13598-36-2) Unless stored in airtight containers, readily absorbs oxygen, forming phosphoric acid. Decomposes above 390°F/198°C, forming phosphine that may ignite spontaneously in air. Incompatible with sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, amides, organic anhydrides, isocyanates, vinyl acetate, alkylene oxides, epichlorohydrin. May increase the explosive sensitivity of nitromethane. Attacks some metals. 

---