A Reiterative Approach to 2,3-Disubstituted Naphthalenes and Anthracenes

Daniel M. Bowles and John E. Anthony*
Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506-0055
Org. Lett., 2000, 2 (1), pp 85–87
DOI: 10.1021/ol991254w
Publication Date (Web): December 16, 1999
Copyright © 2000 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, anthony@pop.uky.edu

Abstract

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Simple bis(bromoethynyl)arenediynes are easily prepared by the desilylative halogenation of the corresponding trimethylsilyl derivatives. Cycloaromatization of these halogenated enediynes leads to the otherwise difficult to prepare 2,3-dibromoarenes in good yield. Alkynylation of the resulting haloaromatic compound regenerates the soluble enediyne system, homologated by one aromatic ring. This iterative methodology can be terminated by the cycloaromatization of the unsubstituted enediyne, providing the simple acene hydrocarbon.

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History

  • Published In Issue January 13, 2000
  • Received November 17, 1999

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