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DOI: 10.1055/sos-SD-008-01267

Mordini, A.; Valacchi, M.Science of Synthesis, (200681438.

As already observed for sodium (, the reductive metalation of carbonhalogen bonds is a troublesome reaction for the preparation of organoalkali compounds. Many precautions need to be taken in order to avoid undesirable parallel reactions (mainly consumption of the newly formed organometallic reagent by the alkyl halide) and decomposition, and, despite these efforts, very poor yields are often observed. Only chlorides are suitable precursors, and hydrocarbon solvents need to be used, both for slowing down any subsequent elimination reaction, and to remove the organometallic compound formed by precipitation.