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Synthesis 1997; 1997(6): 681-684
DOI: 10.1055/s-1997-1392
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4-Lithio-4'-alkylazobenzenes as Convenient Intermediates for the Preparation of Azobenzene Derivatives

T. Koźlecki1 , L. Syper2 , K. A. Wilk3
  • 1Institute of Organic and Polymer Technology, Technical University of Wrocław, Wybrzeże Wyspiańskiego 27, PL-50-370 Wrocław, Poland
  • 2Institute of Organic Chemistry, Biochemistry and Biotechnology, Technical University of Wrocław, Wybrzeże Wyspiańskiego 27, PL-50-370 Wrocław, Poland
  • 3Institute of Organic and Polymer Technology, Technical University of Wrocław, Wybrzeże Wyspiańskiego 27, PL-50-370 Wrocław, Poland, Fax +48(71)203678; E-mail: kaw@itots.ch.pwr.wroc.pl
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Publication Date:
31 December 2000 (online)

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The first successful generation of lithioazobenzenes from bromoazobenzenes utilizing the Köbrich-Buck halogen-lithium exchange is described. The aryl anions formed were trapped with a great variety of different electrophiles (deuterium oxide, acetone, benzaldehyde, 5,5-diethoxypentan-2-al, bromotrimethylsilane and dimethylformamide) to provide the respective 4-substituted azobenzene derivatives.

lithium-bromine exchange - azobenzene derivatives - aromatic electrophilic substitution - elimination-isomerization