Triphenylphosphine dichloride
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Triphenylphosphine dichloride is an organophosphorus compound with the chemical formula Template:Chem2, often abbreviated as Template:Chem2, where Ph is phenyl. It is a chlorinating agent widely used in organic chemistry. Applications include the conversion of alcohols and ethers to alkyl chlorides, the cleavage of epoxides to vicinal dichlorides and the chlorination of carboxylic acids to acyl chlorides.[1]
Structure
In polar solvents such as acetonitrile, Template:Chem2 adopts an ionic phosphonium salt structure, Template:Chem2 (chlorotriphenylphosphonium chloride),[2] whereas in non-polar solvents like diethyl ether it exists as a non-solvated trigonal bipyramidal molecule.[3] Two Template:Chem2 species can also adopt an unusual dinuclear ionic structure—both interacting with a Template:Chem2 via long Cl–Cl contacts.[2]
Synthesis
Triphenylphosphine dichloride is usually prepared fresh by the addition of chlorine to triphenylphosphine.
Both reagents are typically used in solution to ensure the correct stoichiometry.[1]
Template:Chem2 can also be obtained by the reaction of iodobenzene dichloride (Template:Chem2) and triphenylphosphine.[4]
Alternatively, Template:Chem2 can be obtained by chlorination of triphenylphosphine oxide with, for example, phosphorus trichloride, as in Grignard's original 1931 synthesis.[5]
References
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- ↑ Carle, M. S., Shimokura, G. K. and Murphy, G. K. (2016), Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2. Eur. J. Org. Chem., 2016: 3930–3933. {{DOI:10.1002/ejoc.201600714}}
- ↑ Cite error: Script error: No such module "Namespace detect".Script error: No such module "Namespace detect".
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