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Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5) 3 and often abbreviated to P Ph 3 or Ph 3 P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic ...
Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula OP(C 6 H 5) 3, also written as Ph 3 PO or PPh 3 O (Ph = C 6 H 5). It is one of the more common phosphine oxides. This colourless crystalline compound is a common but potentially useful waste product in reactions involving triphenylphosphine.
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The structure of the phosphine oxide is not strongly perturbed by coordination. The geometry at phosphorus remains tetrahedral. The P-O distance elongates by ca. 2%. In triphenylphosphine oxide, the P-O distance is 1.48 Å. [3] In NiCl 2 [OP(C 6 H 5) 3] 2, the distance is 1.51 Å (see figure).
Triphenylphosphine sulfide (IUPAC name: triphenyl-λ 5-phosphanethione) is the organophosphorus compound with the formula (C 6 H 5) 3 PS, usually written Ph 3 PS (where Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents.
Triphenylphosphine selenide is an organophosphorus compound with the formula (C 6 H 5) 3 PSe. It is a white solid which is soluble in most organic solvents. The compound is used in the preparation of other selenium compounds and is itself prepared by the reaction of triphenylphosphine with potassium selenocyanate. [2]
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
Triphenylphosphine phenylimide is the organophosphorus compound with the formula Ph 3 P=NPh (Ph = C 6 H 5). The compound is classified as a phosphanimine. This white solid is soluble in organic solvents. The compound is a prototype of a large class of Staudinger reagents, resulting from the Staudinger reaction.
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