Science of Synthesis

Mordini, A.; Valacchi, M., Science of Synthesis, (2006) 8, 1199.

Older methodologies for the synthesis of alkylsodium reagents are based upon the reductive cleavage of organomercury compounds by sodium.[‌2‌,‌32‌–‌34‌] This method, however, has only a historical interest, and it is likely that it will never become popular due to its many drawbacks. The toxic mercury, which is produced in the reaction, has to be bound in the form of an amalgam in order to push the reversible process to completion. This means that the alkali metal has to be used in large excess (5- to 15-fold), and the reaction usually requires several hours, if not days. For example, the preparation of methylsodium (‌5‌) from sodium and dimethylmercury(II) requires several days at 65°C (‌Scheme 4‌).[‌35‌] Mercury–alkali metal exchange is now used only for the preparation of limited amounts of salt-free organosodium compounds.

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References

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• 8.Meeeee-Meee, (8888) 88/8, 888.