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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 ...
The acyl azide is usually made from the reaction of acid chlorides or anhydrides [6] with sodium azide [7] or trimethylsilyl azide. [8] Acyl azides are also obtained from treating acylhydrazines with nitrous acid. [9] Alternatively, the acyl azide can be formed by the direct reaction of a carboxylic acid with diphenylphosphoryl azide (DPPA ...
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.
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°.
In the laboratory, diphenylphosphine is a common intermediate. It can be deprotonated to give diphenylphosphide derivatives: [2] Ph 2 PH + n BuLi → Ph 2 PLi + n BuH. The preparation of phosphine ligands, Wittig-Horner reagents, and phosphonium salts are commonly accomplished by alkylating diphenylphosphine.
The lithium, sodium, and potassium salts are prepared by reduction of chlorodiphenylphosphine, [1] triphenylphosphine, [2] [3] or tetraphenyldiphosphine with alkali metals (M): (C 6 H 5) 2 PCl + 2 M → (C 6 H 5) 2 PM + MCl (C 6 H 5) 3 P + 2 M → (C 6 H 5) 2 PM + MC 6 H 5 (C 6 H 5) 4 P 2 + 2 M → 2 (C 6 H 5) 2 PM. They can also be obtained by ...
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.
Diphenylphosphine oxide exists in equilibrium with its minor tautomer diphenylphosphinous acid, ((C 6 H 5) 2 POH: (C 6 H 5) 2 P(O)H ⇌ (C 6 H 5) 2 POH. Diphenylphosphine oxide is used in Buchwald-Hartwig coupling reactions to introduce diphenylphosphino substituents.