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Dimethyl Cuprate Undergoes C−C Bond Coupling with Methyliodide in the Gas Phase but Dimethyl Argenate Does Not

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journal contribution
posted on 05.08.2004, 00:00 by Patrick F. James, Richard A. J. O'Hair
Multistage mass spectrometry experiments have been used to synthesize and study the reactions of (CH3)2M- (M = Cu and Ag) with methyl iodide in the gas phase. While the dimethylcuprate ion (M = Cu) reacts with CH3I via C−C bond cross coupling, its silver congener is unreactive. The experimental results are consistent with MP2/6-31++G** ab initio calculations, which reveal that the preferred mechanism for Cu involves the formation of a T-shaped Cu transition state.