Chapter 7. Polyynes Via Alkylidene Carbenes and Carbenoids

  1. Prof. Dr. François Diederich1,
  2. Prof. Dr. Peter J. Stang2 and
  3. Prof. Dr. Rik R. Tykwinski3
  1. Sara Eisler and
  2. Prof. Dr. Rik R. Tykwinski

Published Online: 24 OCT 2005

DOI: 10.1002/3527605487.ch7

Acetylene Chemistry: Chemistry, Biology, and Material Science

Acetylene Chemistry: Chemistry, Biology, and Material Science

How to Cite

Eisler, S. and Tykwinski, R. R. (2004) Polyynes Via Alkylidene Carbenes and Carbenoids, 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.ch7

Editor Information

  1. 1

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

  2. 2

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

  3. 3

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

Author Information

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

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;
  • polyynes;
  • alkylidene carbene and carbenoid;
  • alkyne formation from carbenes and carbenoids;
  • applications;
  • linear conjugated polyynes

Summary

This chapter contains sections titled:

  • Introduction

  • Alkylidene Carbene and Carbenoid Species

  • Alkyne Formation from Carbenes and Carbenoids

    • Synthesis of Acetylenes: the Fritsch–Buttenberg–Wiechell Rearrangement

    • Synthesis of 1,3–Butadiynes

    • Synthesis of 1,3,5–Hexatriynes

    • Tri- and Pentaynes from Free Alkylidene Carbenes

  • Toward applications

    • Natural Products Synthesis

    • Extended Arylenethynylene Derivatives

    • Cyclo[n]carbons

  • Linear Conjugated Polyynes

    • Synthesis of Triisopropylsilyl End-Capped Polyynes

    • Solid-State Characterization

    • Linear Optical Properties

    • Third-Order Nonlinear Optical Properties

  • Conclusions

  • Experimental Procedures

    • General Procedure for Friedel–Crafts Acylation

    • General Procedure for Dibromoolefination

    • General FBW Rearrangement Procedure

    • General Oxidative Coupling Procedure

  • Acknowledgements