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| Names | |||
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| IUPAC name
?
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| Other names
Dichlorotriphenylphosphorane
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| Identifiers | |||
| ChemSpider | |||
| Properties | |||
| C18H15Cl2P | |||
| Molar mass | 333.19 g/mol | ||
| Melting point | 176 °C[1], 85-100 °C[2] | ||
| Related compounds | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triphenylphosphine dichloride, Ph3PCl2, 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.[2]
Synthesis
editTriphenylphosphine dichloride is usually prepared fresh by the addition of chlorine to triphenylphosphine.
Ph3P + Cl2 → Ph3PCl2
Both reagents are typically used in solution to ensure the correct stoichiometry.[2]
Alternatively, Ph3PCl2 can be obtained by chlorination of triphenylphosphine oxide with, for example, phosphorus trichloride, as in Grignard's original 1931 synthesis.[1]
Structure
editIn polar solvents such as acetonitrile or dichloromethane solutions, Ph3PCl2 adopts an ionic structure[3], [Ph3PCl]Cl, whereas in non-polar solvents like diethyl ether it exists as a non-solvated trigonal bipyramidal molecule.[4].
References
edit- ^ a b V. Grignard, J. Savard (1931). Compt. rend. 192: 592–5.
{{cite journal}}: Missing or empty|title=(help) - ^ a b c e-EROS Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289X.rt371
- ^ S. M. Godfrey, C. A. McAuliffe, R. G. Pritchard, J. M. Sheffield (1996). Chem. Commun.: 2521−2522. doi:10.1039/CC9960002521.
{{cite journal}}: Missing or empty|title=(help)CS1 maint: multiple names: authors list (link) - ^ S. M. Godfrey, C. A. McAuliffe, J. M. Sheffield (1998). Chem. Commun.: 921−922. doi:10.1039/a800820e.
{{cite journal}}: Missing or empty|title=(help)CS1 maint: multiple names: authors list (link)