Benzyl potassium

Benzyl potassium
Identifiers
CAS Number	2785-29-7;
CompTox Dashboard (EPA)	DTXSID00454524 ;
Properties
Chemical formula	C7H7K
Appearance	orange solid
	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 with few solvents. It was originally prepared by two-step reaction from p-tolyl sodium:^[1]

(CH₃C₆H₄)₂Hg + 2 Na → 2 CH₃C₆H₄Na + Hg

CH₃C₆H₄Na → KCH₂C₆H₅

The contemporary synthesis involves the reaction of butyllithium, potassium tert-butoxide, and toluene.^[2]

References

^ Gilman, Henry; Pacevitz, Henry A.; Baine, Ogden "Benzylalkali compounds" Journal of the American Chemical Society 1940, vol. 62, pp. 1514-20.
^ 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

[1] Gilman, Henry; Pacevitz, Henry A.; Baine, Ogden "Benzylalkali compounds" Journal of the American Chemical Society 1940, vol. 62, pp. 1514-20.

[2] 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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