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Synthesis 1986; 1986(1): 64-66
DOI: 10.1055/s-1986-31479
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An Easy, High-yield Synthesis of Highly Chlorinated Mono-, Di- and Triarylmethanes

Manuel Ballester* , Juan Riera, Juan Castañer, Concepción Rovira, Olag Armet
  • *Instituto de Química Orgánica Aplicada (C.S.I.C.), C. Jorge Girona Salgado 18-26, 08034 Barcelona, Spain
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Publikationsdatum:
20. August 2002 (online)

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A simple, direct, high-yield Friedel-Crafts synthesis of highly chlorinated, overcrowded αH-aryl, αH-diaryl, and αH-triarylmethanes is described. The latter compounds are most valuable chemical precursors of inert free radicals, which are frequently obtained through otherwise cumbersome, medium-to-low-yield aromatic chlorination of triphenylmethane derivatives. The condensation is performed with aluminium chloride at temperatures ranging from 70 to 160°C. The substrate is a benzene with all its hydrogens flanked by two ortho chlorines. The alkylating component is chloroform, αH-heptachlorotoluene (2a) or αH-undecachlorodiphenylmethane (3a). For comparison, the condensation with a few non-sterically-hindered substrates has also been performed.