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Sheep in wolves′ clothing? Quantum chemical calculations suggest that coordination of DMF to alkylzinc iodides can promote ionisation of the zinciodine bond leading to the formation of solvated alkylzinc cations, as depicted. Such cations can also be detected by ESI-MS measurements. This ionisation may be partly responsible for the compatibility of alkylzinc iodides with acidic protons, as well as the lower reactivity of alkylzinc halides towards electrophiles compared to dialkylzinc reagents.
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Caggiano et al. (2008) studied this question.
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