Phosphorus Oxychloride related reagents

Much the same activity is retained when the nitrogen atoms in the heterocyclic nucleus are shifted around. The convergent scheme to this related compound starts with the acylation of alanine (35-1) with butyryl chloride (35-2). The thus-produced amide (35-3) is then again acylated, this time with the half-acid chloride from ethyl oxalate in the presence of DMAP and pyridine to afford the intermediate (35-4). In the second arm of the scheme, the benzonitrile (35-5) is reacted with the aluminate (35-6), itself prepared from trimethyl aluminum and ammonium chloride, to form the imidate (35-7). Treatment of this intermediate with hydrazine leads to the replacement of one of the imidate nitrogen atoms by the reagent by an addition-elimination sequence to form (35-8). Condensation of this product with (35-4) leads to the formation of the triazine (35-9). Phosphorus oxychloride then closes the second ring... 

Further relation between the hydroxyl groups was discovered by Orekhov and his co-workers (39, 40). When platynecine was treated with a variety of reagents (sulfuric acid, thionyl chloride, phosphorus trichloride, phosphorus pentachloride, or phosphorus oxychloride), it underwent the loss of a molecule of water to form anhydroplatynecine, CgHisNO, b.p. 

Generally, phenyl iV-phenylphosphoramidochloridate and other very similar related organophosphorus reagents e.g. phosphorus oxychloride, phenyl dichlorophosphate, diphenylchlorophos-phate and iV,W -bis(2-oxo-3-oxazolinyl)phosphorodiamidic chloride have been utilised in recent years not only to form symmetrical carboxylic acid anhydrides but also in esterification and thiol esterification reactions although phenyl N-phenylphosphoramidochloridate is not so efficient for the latter two reactions compared to its analogs but is probably the best choice for forming the anhydride. ... 

Related Reagents. Dimethylchloromethyleneammonium Chloride Oxalyl Chloride Phosphorus(III) Chloride Phos-phorus(V) Oxide Phosphorus Oxychloride Thionyl Chloride Triphenylphosphine-Carbon Tetrachloride Triphenylphosphine Dichloride. 

Related Reagents. Bis(trichloromethyl) Carbonate Phos-phorus(V) Oxide Phosphorus Oxychloride-Zinc(II) Chloride Thionyl Chloride p-Tolyl Vinyl Sulfoxide Trichloromethyl Chloroformate. 

---