Download PDF
Synthesis 1986; 1986(1): 64-66
DOI: 10.1055/s-1986-31479
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
20 August 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.