Comparative Studies on the Addition Reactions of the Normant Reagent ("CH3MgBr" + CuBr) and the New Tetrahydrofuran-Soluble Magnesium Methylcuprates MgmCun(CH3)2m+n with Phenylacetylene

Article abstract of DOI:10.1021/jo00338a013

Reactions of phenylacetylene with the Normant reagent ("CH3MgBr" + CuBr) and the THF-soluble magnesium methyl cuprates MgmCun(CH3)2m+n obtained from the reaction of (CH3)2Mg with CuBr have been studied in detail.An attempt to determine the reactive species in Normant reagents was made by studying the rate of reaction of the Normant reagent with phenylacetylene compared to the rate observed with various magnesium methylcuprates.Cu4Mg(CH3)6 and Cu6Mg(CH3)8 have been shown to be the most probable candidates responsible for reactions involving the Normant reagent with alkynes.The effect of MgBr2 and LiBr on the reactivity and the product selectivity has also been studied.