Download PDF
Synlett 1990; 1990(8): 467-468
DOI: 10.1055/s-1990-21129
letter
© 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.

Chromium Mediated Organic Synthesis: The Introduction of 1,1-Dimethylallyl and Linalyl Groups on to Arenes

Neil Mathews* , David A. Widdowson
  • *Department of Chemistry, Imperial College, London SW7 2AY, England
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The synthesis of 1,1-dimethylallyl-substituted benzene-and anisoletricarbonylchromium(0) complexes was achieved in a two- or three-step sequence by the copper catalysed coupling of the lithiated arenetricarbonylchromium(0) complexes with allyl bromide followed by a double benzylic alkylation with potassium tert-butoxide/methyl iodide. For the linalyl substituted complexes the alkylations were sequential homoprenylation and methylation. Alternatively, palladium catalysed cross coupling with 2-bromo-2-butene followed by γ-deprotonation of the 1-aryl-1-propene complexes provided a more direct approach to the anionic intermediates involved.

      >