Reaction of 2-Methylanisole with TpMe2Ir(C6H5)2(N2): A Comprehensive Set of Activations

The thermal activation of 2-methylanisole (60 degrees C) by the Ir(III) complex Tp(Me2)Ir(C6H5)(2)(N-2) (1; Tp(Me2) = hydrotris(3,5-dimethylpyrazoly)borate) yielded a mixture of hydride complexes derived from each of the possible activation processes that might be anticipated in view of the previously investigated reactions of anisole and 2,6-dimethylanisole. Four isomeric species resulted from this reaction, namely hydride-carbene 6, emanating from two C(sp(3))-H and one C(sp(2))-H bond activation, hydride-alkylidene 7, whose formation requires in addition cleavage of the O-CH3 bond and the formation of a new C-C bond, and hydride-alkene derivative 4 and its hydride-alkylidene tautomer 3-Me, generated through somewhat related rearrangements. The appearance of these products may be rationalized on the basis of the reactivity previously ascertained for anisole and 2,6-dimethylanisole.