Benzyl potassium: Difference between revisions
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{{Chembox |
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| Name = |
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| ImageFile = Kbenzyl.svg |
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| ImageSize = |
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| ImageSize = 100px |
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| OtherNames = Potassium benzyl |
| OtherNames = Potassium benzyl |
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| SystematicName = |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| CASNo = 2785-29-7 |
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| PubChem = 11083915 |
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| ChemSpiderID = 10675000 |
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| SMILES = [K]Cc1ccccc1 |
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| InChI = 1/C7H7.K/c1-7-5-3-2-4-6-7;/h2-6H,1H2;/rC7H7K/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 |
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| InChIKey = OQLLVOGBAKFMIS-QPGMTJJQAI |
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| StdInChI = 1S/C7H7.K/c1-7-5-3-2-4-6-7;/h2-6H,1H2; |
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| StdInChIKey = OQLLVOGBAKFMIS-UHFFFAOYSA-N }} |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=7|H=7|K=1 |
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| Formula = C<sub>7</sub>H<sub>7</sub>K |
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| MolarMass = 130.23 |
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| Density = |
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| Section3 = {{Chembox Hazards |
| Section3 = {{Chembox Hazards |
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| MainHazards = Ignites in air |
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''' |
'''Benzylpotassium''' is an [[organopotassium compound]] with the formula C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>K, 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. |
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==Synthesis== |
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One early synthesis proceeds by two-step [[transmetallation reaction]] by ''p''-tolylpotassium:<ref>{{cite journal |doi = 10.1021/ja01863a054|title = Benzylalkali Compounds1|journal = Journal of the American Chemical Society|volume = 62|issue = 6|pages = 1514|year = 1940|last1 = Gilman|first1 = Henry|last2 = Pacevitz|first2 = Henry A|last3 = Baine|first3 = Ogden}}</ref> |
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A modern synthesis involves the reaction of [[butyllithium]], [[potassium tert-butoxide]], and [[toluene]].<ref>Philip J. Bailey, Robert A. Coxall, Caroline M. Dick, Sylvie Fabre, Louise C. Henderson, |
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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}}</ref> 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. |
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A modern synthesis involves the reaction of [[butyllithium]], [[potassium tert-butoxide|potassium ''tert''-butoxide]], and [[toluene]].<ref>{{cite journal | doi = 10.1016/0022-328X(87)80117-1| title = Lithium-potassium exchange in alkyllithium/potassium t-pentoxide systems| journal = Journal of Organometallic Chemistry| volume = 326| pages = 1| year = 1987| last1 = Lochmann| first1 = L| last2 = Trekoval| first2 = J}}</ref> 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. |
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==References== |
==References== |
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<references /> |
<references /> |
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[[Category:Potassium compounds]] |
[[Category:Potassium compounds]] |
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[[Category:Benzyl compounds]] |
Latest revision as of 13:26, 17 July 2024
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Names | |
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Other names
Potassium benzyl
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C7H7K | |
Molar mass | 130.231 g·mol−1 |
Appearance | Orange solid |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Ignites in air |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]One early synthesis proceeds by two-step transmetallation reaction by 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
[edit]- ^ Gilman, Henry; Pacevitz, Henry A; Baine, Ogden (1940). "Benzylalkali Compounds1". Journal of the American Chemical Society. 62 (6): 1514. doi:10.1021/ja01863a054.
- ^ 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.