Communication

Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes)†

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

Article first published online: 30 AUG 2002

DOI: 10.1002/1521-3773(20020902)41:17<3223::AID-ANIE3223>3.0.CO;2-G

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 41, Issue 17, pages 3223–3227, September 2, 2002

Additional Information

How to Cite

Han, S., Bond, A. D., Disch, R. L., Holmes, D., Schulman, J. M., Teat, S. J., Vollhardt, K. P. C. and Whitener, G. D. (2002), Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes). Angewandte Chemie International Edition, 41: 3223–3227. doi: 10.1002/1521-3773(20020902)41:17<3223::AID-ANIE3223>3.0.CO;2-G

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. We are grateful to Professor P. von R. Schleyer for communicating unpublished data. 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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Two plus two plus two times two: A double cobalt-catalyzed cycloisomerization was used to convert appropriate hexaynes into hydrocarbons 1 and 2. Their X-ray structures reveal pronounced helical topologies, but their barriers to enantiomerization are low compared to those of the helicenes.

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