Benzyl potassium
| Names | |
|---|---|
| Other names
Potassium benzyl | |
| Identifiers | |
| 2785-29-7 | |
| ChemSpider | 10675000 |
| Jmol interactive 3D | Image |
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| Properties | |
| C7H7K | |
| Molar mass | 130.23 |
| Appearance | orange solid |
| Hazards | |
| Main hazards | ignites in air |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Benzyl potassium is an organopotassium compound with the formula C6H5CH2K. It is an orange solid that is so extremely basic that it is compatible only with hydrocarbon solvents.
Synthesis
One early synthesis proceeds by two-step transmetallation reaction via p-tolylpotassium:[1]
- (CH3C6H4)2Hg + 2 K → 2 CH3C6H4K + Hg
- CH3C6H4K → KCH2C6H5
A modern synthesis involves the reaction of butyllithium, potassium tert-butoxide, and toluene.[2] Although potassium hydride can also be used as a strong base for preparing potassium salts, benzyl potassium has the advantage of being molecular and hence more fast-acting.
References
- ↑ Gilman, Henry; Pacevitz, Henry A.; Baine, Ogden "Benzylalkali Compounds" Journal of the American Chemical Society 1940, vol. 62, pp. 1514-20. doi:10.1021/ja01863a054
- ↑ Philip J. Bailey, Robert A. Coxall, Caroline M. Dick, Sylvie Fabre, Louise C. Henderson, Christian Herber, Stephen T. Liddle, Daniel Loroño-Gonzālez, Andrew Parkin, Simon Parsons "The First Structural Characterisation of a Group 2 Metal Alkylperoxide Complex: Comments on the Cleavage of Dioxygen by Magnesium Alkyl Complexes" Chemistry, European Journal 2003, vol. 9, pp. 4820-4828. doi:10.1002/chem.200305053
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