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It is now suggested that this reaction proceeds through the intermediate mixed anhydride, resulting from attack by the nucleophilic carboxylate anion on the phosphorus atom, with expulsion of the azide ion. The latter then attacks the carbonyl carbon atom, to give the acyl azide and loss of the diphenylphosphate anion, known to be a good ...
For example, in the presence of concentrated hydrochloric acid at 100 °C, diphenylphosphine adds to the carbon atom in benzaldehyde to give (phenyl-(phenylmethyl)phosphoryl)benzene. Ph 2 PH + PhCHO → Ph 2 P(O)CH 2 Ph. Compared to tertiary phosphines, diphenylphosphine is weakly basic. The pKa of the protonated derivative is 0.03: [4]
The azide functional group can be shown by two resonance structures. An organic azide is an organic compound that contains an azide (– N 3) functional group. [1] Because of the hazards associated with their use, few azides are used commercially although they exhibit interesting reactivity for researchers.
Diphenyl phosphite is a diorganophosphite with the formula (C 6 H 5 O) 2 P(O)H. The molecule is tetrahedral. It is a colorless viscous liquid. The compounds can be prepared by treating phosphorus trichloride with phenol. Many analogues can be prepared similarly.
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 . It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide . [ 4 ]
With water, the salts convert to diphenylphosphine: [3] (C 6 H 5) 2 PLi + H 2 O → (C 6 H 5) 2 PH + LiOH. With halocarbons, the salts react to give tertiary phosphines: [4] (C 6 H 5) 2 PM + RX → (C 6 H 5) 2 PR + MX. When treated with metal halides, lithium diphenylphosphide gives transition metal phosphido complexes.
Chlorodiphenylphosphine is used in the synthesis of sodium diphenylphosphide via its reaction with sodium metal in refluxing dioxane. [5] Ph 2 PCl + 2 Na → Ph 2 PNa + NaCl. Diphenylphosphine can be synthesized in the reaction of Ph 2 PCl and LiAlH 4, the latter usually used in excess. [6] 4 Ph 2 PCl + LiAlH 4 → 4 Ph 2 PH + LiCl + AlCl 3
Phenyl azide is an organic compound with the formula C 6 H 5 N 3. It is one of the prototypical organic azides. It is a pale yellow oily liquid with a pungent odor. The structure consists of a linear azide substituent bound to a phenyl group. The C−N=N angle is approximately 116°.