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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.