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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 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.
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 ...
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°.
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]
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 ]
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.
Many coordination complexes of dppe are known, and some are used as homogeneous catalysts. Dppe is almost invariably chelating, although there are examples of monodentate (e.g., W(CO) 5 (dppe)) and of bridging behavior. [5] The natural bite angle is 86°. [6]