Abstract

The reduction of meta-methyl-substituted iodobenzene with activated calcium in tetrahydrofuran (THF) yields [(3-MeC6H4)CaI(thf)4] (1) and [(3,5-Me2C6H3)CaI(thf)4] (2). The reaction of 3-halo-1-iodobenzene with calcium powder leads to the formation of the corresponding post-Grignard reagents [(3-XC6H4)CaI(thf)4] [X = F (3), Cl (4), Br (5), and I (6)]. The synthesis of the thf adducts of 3-methoxyphenylcalcium iodide (7) and β-naphthylcalcium iodide (8) follows the same strategy. All post-Grignard reagents show a characteristic low-field shift for the calcium-bound carbon atoms in 13C NMR spectra. The molecular structures of 1, 2, 4, and 8 show distorted octahedral environments for the calcium centers with the aryl and halide anions in a trans arrangement.

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