Chapter 18. Arynes and Heteroarynes

  1. Professor Saul Patai
  1. Harold Hart

Published Online: 29 JUL 2004

DOI: 10.1002/0470024771.ch18

Triple Bonded Functional Groups (1994)

Triple Bonded Functional Groups (1994)

How to Cite

Hart, H. (1994) Arynes and Heteroarynes, in Triple Bonded Functional Groups (1994) (ed S. Patai), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470024771.ch18

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, Michigan State University, 320 Chemistry Building, East Lansing, Michigan 48824–1322, USA

Publication History

  1. Published Online: 29 JUL 2004
  2. Published Print: 31 OCT 1994

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Professor Saul Patai and
  2. Professor Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471935599

Online ISBN: 9780470024775

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Summary

This chapter contains sections titled:

  • Introduction

  • The Structure of Benzyne

    • Infrared Spectrum

    • Other Spectra

    • Theoretical Calculations

    • Heat of Formation

  • Generation of Arynes

    • Benzyne

      • Type A1

      • Type A2

      • Type B

      • Type C

    • Other Benzynes

    • Benzynes as Intermediates

  • The Benzyne–Cyclopentylidenecarbene Rearrangement

  • Cycloaddition Reactions of Arynes

    • General Remarks

    • Diels–Alder Cycloadditions

      • Acyclic Dienes

      • Cyclic Dienes

      • Benzenoid Aromatics

      • Five-membered Aromatic Heterocycles

      • Six-membered Heterocycles

    • [2+2] Cycloadditions

    • 1, 3-dipolar Cycloadditions

    • Miscellaneous Cycloadditions

    • Cycloadditions with Two or More Aryne Intermediates

  • Nucleophilic Addition to Arynes

    • General Remarks

    • Carbon Nucleophiles

    • Other Nucleophiles

    • Multiple and Tandem Aryne Reactions via Nucleophiles

  • Natural Products via Arynes

    • Intramolecular Cycloadditions

    • Intermolecular Cycloadditions

      • Aporphinoids

      • Protoberberines

      • Benzo[C]Phenanthridines

      • Aryl C-glycosides

  • Heteroarynes

    • Six-membered Heteroarynes

      • Didehydropyridines

        • Structure

        • Generation

        • Thermal Rearrangements in the Gas Phase

        • Cycloadditions

        • Nucleophilic Additions

      • Didehydrodiazines

    • Five-membered Heteroarynes

  • Omissions

  • References