Benzyl potassium
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Potassium benzyl
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3D model (JSmol)
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| Properties | |
| C7H7K | |
| Molar mass | 130.231 g·mol−1 |
| Appearance | Orange solid |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
Benzylpotassium is an organopotassium compound with the formula C6H5CH2K, an orange powder. Like organo-alkali metal reagents in general, benzyl potassium is highly reactive, so much so that it reacts with most solvents. It is highly air sensitive.
Synthesis
One early synthesis proceeds by two-step transmetallation reaction by p-tolylpotassium:[1]
- Page Module:Chem2/styles.css has no content.(CH3C6H4)2Hg + 2 K → 2 CH3C6H4K + Hg
- Page Module:Chem2/styles.css has no content.CH3C6H4K → KCH2C6H5
A modern synthesis involves the reaction of butyllithium, potassium tert-butoxide, and toluene.[2]
The structure of the related diphenylmethane derivative has been confirmed by X-ray crystallography.[3]
References
- ^ Page Module:Citation/CS1/styles.css has no content.Gilman, Henry; Pacevitz, Henry A; Baine, Ogden (1940). "Benzylalkali Compounds1". Journal of the American Chemical Society. 62 (6): 1514. doi:10.1021/ja01863a054.
- ^ Page Module:Citation/CS1/styles.css has no content.Lochmann, L; Trekoval, J (1987). "Lithium-potassium exchange in alkyllithium/potassium t-pentoxide systems". Journal of Organometallic Chemistry. 326: 1. doi:10.1016/0022-328X(87)80117-1.
- ^ Page Module:Citation/CS1/styles.css has no content.Schumann, Herbert; Freckmann, Dominique M. M.; Dechert, Sebastian (2006). "Organometallic Compounds of the Lanthanides. 179. Synthesis and Structural Characterization of a Mixed Alkyl (Benzhydryl, Trimethylsilylmethyl) Lutetium Complex". Organometallics. 25 (10): 2696–2699. doi:10.1021/om0601201.
