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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 (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 chemistry.
A phosphine sulfide is an organophosphorus compound with the formula R 3 PS. They are typically colorless, air-stable solids. A common example of a tertiary phosphine sulfide is triphenylphosphine sulfide. Phosphine sulfides are sometimes intermediates in the synthesis of tertiary phosphines. Phosphine sulfides are tetrahedral.
The methylation of triphenylphosphine is the first step in the preparation of the Wittig reagent. Illustrative phosphorus(V) compounds: the phosphonium ion P(CH 2 OH) 4 +, two resonance structures for the Wittig reagent Ph 3 PCH 2, and pentaphenylphosphorane, a rare pentaorganophophorus compound. The parent phosphorane (σ 5 λ 5) is PH 5 ...
The use of triphenylphosphine, thiourea, zinc dust, or dimethyl sulfide produces aldehydes or ketones. While the use of sodium borohydride produces alcohols. (R group can also be hydrogens) The use of hydrogen peroxide can produce carboxylic acids. Amine N-oxides produce aldehydes directly. [8]
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.
First phosphine imine-forming reaction is conducted involving treatment of the azide with the phosphine. The intermediate, e.g. triphenylphosphine phenylimide, is then subjected to hydrolysis to produce a phosphine oxide and an amine: R 3 P=NR' + H 2 O → R 3 P=O + R'NH 2. The overall conversion is a mild method of reducing an azide to an amine.
C 6 H 5) 3 CSSH behaves as a source of sulfur, illustrated by its reaction with triphenylphosphine to give triphenylphosphine sulfide and triphenylmethanethiol: (C 6 H 5) 3 CSSH + P(C 6 H 5) 3 → (C 6 H 5) 3 CSH + SP(C 6 H 5) 3