The bulky m-terphenyl phenol Ar*OH 1 (Ar* = C6H3-2,6-Mes2, Mes = 2,4,6-trimethylphenyl) was synthesized via the treatment of Ar*Li with nitrobenzene. The phenol 1 is prepared in modest to good yield using this method. Attempts were also made to prepare 1 through oxidation of the bulky boronic acid Ar*B(OH)2 with Oxone®, but this reaction was not suitable for preparative-scale reactions. Side products of the reaction between Ar*Li and nitrobenzene were identified as Ar*[N(O)Ph] and [C6H5N(O)]2 and were characterized by X-ray crystallography and EPR spectroscopy. A variety of main-group and transition-metal complexes of Ar*OH were prepared, namely Sn(OAr*)2, Ge(OAr*)2, [N(SiMe3)2]Ge(OAr*), [Me2Al(OAr*)]2, and Ti(NMe2)(OAr*)2. All compounds were characterized spectroscopically and most were studied by single-crystal X-ray diffraction as well.Key words: m-terphenyl, main-group compounds, X-ray crystallography, multinuclear NMR spectroscopy, EPR spectroscopy.

The organometallic dianions diethyltetrachlorodizincate, [Et(Cl)Zn(μ-Cl) 2 Zn(Cl)Et], and ethyltribromozincate, [EtZnBr 3 ], have been isolated from reaction mixtures containing diethylzinc and a tetraphenylphosphonium halide (X = Cl or Br). Evidence for these anions had previously been reported using mass spectrometry. The ions may have importance in the solution structure of organozinc reagents used extensively in organic synthesis.

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The bulky m-terphenyl benzyl alcohols ArCH2OH (Ar = 2,4,6-triphenylphenyl) 1 and Ar*CH2OH (Ar* = C6H3-2,6-Mes2, Mes = 2,4,6-trimethylphenyl) 2 were synthesized via treatment of the corresponding aryllithium salt with DMF followed by NaBH4 reduction. A zinc complex of 1 was prepared and contains a rather uncommon trigonal planar geometry for a zinc organometallic compound. All compounds were characterized spectroscopically and were studied by single crystal X-ray diffraction techniques.