Communication

Total Syntheses of Angular [7]-, [8]-, and [9]Phenylene by Triple Cobalt-Catalyzed Cycloisomerization: Remarkably Flexible Heliphenes†

  1. Sangdon Han Dr.1,
  2. D. Ryan Anderson1,
  3. Andrew D. Bond Dr.2,
  4. Hiufung V. Chu1,
  5. Raymond L. Disch Prof.3,
  6. Daniel Holmes Dr.1,
  7. Jerome M. Schulman Prof.3,
  8. Simon J. Teat Dr.4,
  9. K. Peter C. Vollhardt Prof.1,
  10. Glenn D. Whitener1

Article first published online: 30 AUG 2002

DOI: 10.1002/1521-3773(20020902)41:17<3227::AID-ANIE3227>3.0.CO;2-T

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 41, Issue 17, pages 3227–3230, September 2, 2002

Additional Information

How to Cite

Han, S., Anderson, D. R., Bond, A. D., Chu, H. V., Disch, R. L., Holmes, D., Schulman, J. M., Teat, S. J., Vollhardt, K. P. C. and Whitener, G. D. (2002), Total Syntheses of Angular [7]-, [8]-, and [9]Phenylene by Triple Cobalt-Catalyzed Cycloisomerization: Remarkably Flexible Heliphenes. Angewandte Chemie International Edition, 41: 3227–3230. doi: 10.1002/1521-3773(20020902)41:17<3227::AID-ANIE3227>3.0.CO;2-T

Author Information

  1. 1

    Center for New Directions in Organic Synthesis Department of Chemistry, University of California at Berkeley and the Chemical Sciences Division, Lawrence Berkeley National Laboratory Berkeley, CA 94720-1460 (USA) Fax: (+1) 510-643-5208

  2. 2

    University of Cambridge, Department of Chemistry Lensfield Road, Cambridge, CB2 1EW (UK)

  3. 3

    Department of Chemistry The City University of New York, Queens College Flushing, NY 11367 (USA)

  4. 4

    CLRC Daresbury Laboratory, Warrington Cheshire, WA4 4AD (UK)

  1. †

    This study was facilitated by the National Science Foundation (CHE-0071887), the Engineering and Physical Sciences Research Council (EPSRC, GR/R08919), and the Biotechnology and Biological Sciences Research Council (BBSRC, 8/B11586). G.D.W. was supported by NSF and Bayer-Miles Inc. predoctoral fellowships. The Center for New Directions in Organic Synthesis is supported by Bristol-Myers Squibb as a Sponsoring Member and Novartis as a Supporting Member.

Publication History

  1. Issue published online: 30 AUG 2002
  2. Article first published online: 30 AUG 2002
  3. Manuscript Received: 24 APR 2002

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Keywords:

  • antiaromaticity;
  • cyclotrimerization;
  • helical structures;
  • phenylenes;
  • small ring systems

Graphical Abstract

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Six of the final cyclobutadiene rings in angular [8]phenylene and [9]phenylene (1) are closed in an unprecedented cobalt-catalyzed triple cyclization of appropriate nonaynes. These strained products are the largest known phenylenes and display unusual configurational lability. Their synthesis has enabled a first estimate of the properties of the hypothetical polyheliphene.

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