Phosphorus oxide-acetonitrile

Acidic reagents seem to offer milder conditions. Dehydration reactions forming cyanides can be performed with phosgene [1049-1052], diphosgene [1053-1055], triphosgene [1056], phenyl chloroformate [1057], oxalyl chloride [1058, 1059], tri-chloroacetyl chloride [1060-1062], acetic anhydride [1063-1074], TFAA [1075-1082], phosphorus oxides [1083-1088], phosphorus oxychloride [1089-1098], phosphorus pentachloride [1099], triphenylphosphine/haloalkanes [1100-1103], thionyl chloride [1104-1118], p-tosyl chloride [1119-1124], triflic anhydride [1125-1127], chlorosulfonyl isocyanate [1128], the Burgess reagent [1129], phenyl chloro-thionoformate [1130], cyanuric chloride [1131-1134], carbodiimides [1135, 1136], CDC [1137], PyBOP [1138], AlCU/Nal [1139], and acetonitrile/aldehyde [1140], and by pyrolysis [1141]. 

The extremely violent interaction of phosphorus(V) oxide and cone, hydrogen peroxide to give peroxomonophosphoric acid may be moderated by using acetonitrile as a diluent. 

Indium Iodine Acetonitrile, nitrogen dioxide, mercury(II) bromide, sulfur Acetaldehyde, acetylene, aluminum, ammonia (aqueous or anhydrous), antimony, bromine pentafluoride, carbides, cesium oxide, chlorine, ethanol, fluorine, formamide, lithium, magnesium, phosphorus, pyridine, silver azide, sulfur trioxide... 

In a 1-L three-necked round-bottomed flask and under an atmosphere of nitrogen, a suspension of Os3(CO)12 (0.5 g, 0.55 mmol)4 is prepared in acetonitrile (750 mL), freshly distilled from a slurry of phosphorus pentoxide under nitrogen. To ensure dissolution of the maximum amount of Os3(CO)12, the suspension is heated under reflux for 1 h. The solution is then allowed to cool to room temperature, and under a nitrogen atmosphere, a solution of freshly sublimed, dry trimethylamine oxide (42 mg, 0.55 mmol) in acetonitrile (200 mL) is added to the stirred suspension over a period of 4h using a pressure-equalized dropping funnel. 

Organic constituents that may be found in ppb levels in WP/F smoke include methane, ethylene, carbonyl sulfide, acetylene, 1,4-dicyanobenzene, 1,3-dicyanobenzene, 1,2-dicyanobenzene, acetonitrile, and acrylonitrile (Tolle et al. 1988). Since white phosphorus contains boron, silicon, calcium, aluminum, iron, and arsenic in excess of 10 ppm as impurities (Berkowitz et al. 1981), WP/F smoke also contains these elements and possibly their oxidation products. The physical properties of a few major compounds that may be important for determining the fate of WP/F smoke in the environment are given in Table 3-3. 

Solutions of KO2 and l8-crown-6 in DMSO cause oxidation of the solvent to die sulfone. The phosphorus-containing peroxy anion (EtO)2P03" obtained on reaction of KO2 widi diefiiyl chlorophosphate [(EtO)2POCl] in acetonitrile has been used to prepare sulfones from sulfoxides at 20 C. Similarly, various sulfoxides are readily oxidized chemoselectively to the sulfones in high yields by 2-nitrobenzene peroxysulfur intermediate (26) generated in situ from 2-nitrobenzenesulfonyl chloride and KO2 (Scheme 8 Ar = 2-N02C6H4). ... 

Tsuge, O., Kanemasa, S., and Suga, H., Synthesis of a new phosphorus-functionalized nitrile oxide, a-(diethylphosphono)acetonitrile oxide, and cycloaddition leading to 3-(diethylphosphonomethyl)-A -isoxazolines, Chem. Lett., 183, 1986. 

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