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Composition of the Grignard Reagent

Nature volume 165, page 485 (1950)Cite this article

Abstract

IN 1912 Jolibois1 suggested that the formula of the Grignard reagent was R2Mg.MgX2, and since that time there have been several controversial papers dealing with experimental evidence for and against this idea. The work of W. Schlenk and W. Schlenk, jun.2,3, in which the halogen was entirely precipitated from ether solutions of the Grignard reagent with dioxane, leaving dialkylmagnesium, led them to favour a slow equilibrium in the reaction as the best explanation of the results obtained. This idea of the composition of the Grignard reagent has been popularly held ever since, in spite of many reasons for doubting how anything so simple can fit all the complex results obtained—for example, those of Noller and White4, in which dialkylmagnesium returned to the solution on further shaking the precipitate with the solution after precipitation.

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References

  1. Jolibois, C.R. Acad. Sci., Paris, 155, 353 (1912).

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  2. Schlenk, W., and Schlenk, W., jun., Ber., 62, 920 (1929).

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  3. Schlenk, W., jun., Ber., 64B, 734 (1931).

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  4. Noller, C. R., and White, W. R., J. Amer. Chem. Soc., 59, 1354 (1937).

    Article  CAS  Google Scholar 

  5. Brugger. J. E., M.S. Thesis, Penn. State College (1946).

  6. This apparatus was essentially like that of La Mer and Reed (J. Amer. Chem. Soc., 52, 3098; 1930), with the fraction which had reacted down the tube measured by the temperature-rise indicated by suitably placed thermocouples.

  7. Aston, J. G., and Bernhard, S. A. (to be published)

  8. Aston, J. G., and Kennedy, R. M. (to be published).

  9. Evans, W. V., and Lee, F. H., J. Amer. Chem. Soc., 56, 654 (1934).

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Authors and Affiliations

  1. Department of Chemistry, School of Chemistry and Physics, Pennsylvania State College, Pa.

    J. G. ASTON & S. A. BERNHARD

Authors
  1. J. G. ASTON
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  2. S. A. BERNHARD
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ASTON, J., BERNHARD, S. Composition of the Grignard Reagent. Nature 165, 485 (1950). https://doi.org/10.1038/165485a0

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