Chapter 8. Macrocycles Based on Phenylacetylene Scaffolding

  1. Prof. Dr. François Diederich3,
  2. Prof. Dr. Peter J. Stang4 and
  3. Prof. Dr. Rik R. Tykwinski5
  1. Carissa S. Jones1,
  2. Matthew J. O'Connor1 and
  3. Michael M. Haley2

Published Online: 24 OCT 2005

DOI: 10.1002/3527605487.ch8

Acetylene Chemistry: Chemistry, Biology, and Material Science

Acetylene Chemistry: Chemistry, Biology, and Material Science

How to Cite

Jones, C. S., O'Connor, M. J. and Haley, M. M. (2004) Macrocycles Based on Phenylacetylene Scaffolding, in Acetylene Chemistry: Chemistry, Biology, and Material Science (eds F. Diederich, P. J. Stang and R. R. Tykwinski), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527605487.ch8

Editor Information

  1. 3

    Laboratorium für Organische Chemie, ETH Hönggerberg, HCI, CH-8093 Zürich, Switzerland

  2. 4

    Department of Chemistry, University of Utah, 315S 1400E, Rm. 2020, 84112 Salt Lake City, USA

  3. 5

    Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Author Information

  1. 1

    Department of Chemistry and the Materials Science Institute, 1253 University of Oregon, Eugene, Oregon 97403-1253, USA

  2. 2

    Department of Chemistry, 1253 University of Oregon, Eugene, Oregon 97403-1253, USA

Publication History

  1. Published Online: 24 OCT 2005
  2. Published Print: 14 DEC 2004

ISBN Information

Print ISBN: 9783527307814

Online ISBN: 9783527605484

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Keywords:

  • acetylene chemistry;
  • biology and material science;
  • macrocycles;
  • phenylacetylene scaffolding;
  • synthetic strategies;
  • phenylacetylene macrocycles;
  • phenyldiacetylene macrocycles;
  • phenyltriacetylene macrocycles;
  • phenyltetraacetylene macrocycles;
  • phenyloligoacetylene macrocycles;
  • experimental

Summary

This chapter contains sections titled:

  • Introduction

  • Synthetic Strategies

    • Intermolecular Approach

    • Intramolecular Approach

    • Comparison of the Two Pathways

  • Phenylacetylene Macrocycles

    • Ortho PAMs

    • Meta-PAMs

    • Para-PAMs

    • Mixed PAMs

  • Phenyldiacetylene Macrocycles

    • Ortho-PDMs

    • Meta-PDMs

    • Para-PDMs

    • Mixed PDMs

  • Phenyltriacetylene Macrocycles

  • Phenyltetraacetylene Macrocycles

  • Phenyloligoacetylene Macrocycles

  • Conclusions

  • Experimental

    • Preparation of 8 from [(t-BuO)3W≡Ct-Bu)] Catalysis of 13

    • Synthesis of 8 and 10 from Copper (2-Iodophenyl)acetylide

    • Preparation of 31 by Pd-Catalyzed Cyclization of 29

    • Preparation of 122 by Pd-Mediated Cyclization of 136

    • Synthesis of 148 from 149 and Mo(CO)6

    • Preparation of 189 and 190 from 1,2-Diiodotetrafluorobenzene under Hay Conditions

    • Preparation of 1 by Deprotection and Cyclization of 223

    • Synthesis of 304 by Photolysis of Dewar Benzene 305

    • Preparation of 332 and 333 by Deprotection/Cyclization of 335 in situ

  • Acknowledgements