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Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula P O Cl 3.It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride.
Phosphorus trichloride is prepared industrially by the reaction of chlorine with white phosphorus, using phosphorus trichloride as the solvent. In this continuous process PCl 3 is removed as it is formed in order to avoid the formation of PCl 5. P 4 + 6 Cl 2 → 4 PCl 3
The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5):
PCl 5 is prepared by the chlorination of PCl 3. [10] This reaction is used to produce around 10,000 tonnes of PCl 5 per year (as of 2000). [6] PCl 3 + Cl 2 ⇌ PCl 5 (ΔH = −124 kJ/mol) PCl 5 exists in equilibrium with PCl 3 and chlorine, and at 180 °C the degree of dissociation is about 40%. [6]
Oxalyl chloride was first prepared in 1892 by the French chemist Adrien Fauconnier, who treated diethyl oxalate with phosphorus pentachloride. [5] It can also be prepared by treating oxalic acid with phosphorus pentachloride.
The most common reaction mechanism of the Beckmann rearrangement consists generally of an alkyl migration anti-periplanar to the expulsion of a leaving group to form a nitrilium ion. This is followed by solvolysis to an imidate and then tautomerization to the amide: [6] Beckmann rearrangement mechanism
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The Vilsmeier reagent is an organic compound with the formula [(CH 3) 2 NCHCl]Cl. It is a salt consisting of the N,N-dimethyliminium cation ([(CH 3) 2 N=CHCl] +) and chloride anion.