Arene-Metal Complexes. 12. Reaction of (η6-Benzene)tricarbonylchromium with n-Butyllithium

Article abstract of DOI:10.1021/jo01301a001

The reaction of (η⁶-benzene)tricarbonylchromium with n-butyllithium in tetrahydrofuran at -20 deg C results in the formation of an intermediate which may be quenched by the addition of methyl iodide or iodine to yield (toluene)tricarbonylchromium or (iodobenzene)tricarbonylchromium in 50 or 26percent yield,respectively.The chemistry and the ¹H NMR spectrum of this intermediate are consistent with its assignment as (η⁶-phenyllithium)tricarbonylchromium.If this intermediate is allowed to warm to 0 deg C in the presence of an excess of n-butyllithium,n-butylbenzene is obtained in 80percent yield.Mechanistic details are discussed.