Chapter 4. [N]Phenylenes: a Novel Class of Cyclohexatrienoid Hydrocarbon

  1. Prof. Michael M. Haley2 and
  2. Prof. Rik R. Tykwinski3
  1. Ognjen Š. Miljanić and
  2. K. Peter C. Vollhardt

Published Online: 13 JUN 2006

DOI: 10.1002/3527607994.ch4

Carbon-Rich Compounds: From Molecules to Materials

Carbon-Rich Compounds: From Molecules to Materials

How to Cite

Miljanić, O. Š. and Vollhardt, K. P. C. (2006) [N]Phenylenes: a Novel Class of Cyclohexatrienoid Hydrocarbon, in Carbon-Rich Compounds: From Molecules to Materials (eds M. M. Haley and R. R. Tykwinski), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527607994.ch4

Editor Information

  1. 2

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

  2. 3

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

Author Information

  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, California 94720-1460, USA

Publication History

  1. Published Online: 13 JUN 2006
  2. Published Print: 6 FEB 2006

ISBN Information

Print ISBN: 9783527312245

Online ISBN: 9783527607990

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Keywords:

  • [N]phenylenes;
  • cyclohexatrienoid hydrocarbon;
  • preparation of phenylenes;
  • comparative reactivity of the phenylenes;
  • physical properties of the phenylenes

Summary

This chapter contains sections titled:

  • Introduction

  • Preparation of Phenylenes

    • Early Synthetic Strategies

    • Syntheses of New Phenylenes

      • Angular and Helical Phenylenes

      • Zigzag Phenylenes

      • Phenylenes with Mixed Topology: the “Bent” Isomers

      • Branched Phenylenes

      • Circular Phenylenes

  • Comparative Reactivity of the Phenylenes

    • Hydrogenation

    • Oxacyclopropanation and Cyclopropanation

    • [4+2]Cycloadditions

    • Flash Vacuum Pyrolysis

    • Interaction with Organometallic Fragments

  • Physical Properties of the Phenylenes

    • Structural Properties

    • Magnetic Properties

    • Energetic Properties

  • Conclusion and Outlook

  • Experimental: Selected Procedures

    • Preparation of Bis(trimethylsilyl) Zigzag [4]Phenylene: A One-pot Intra- and Intermolecular [CpCo(CO)2]-Mediated Cyclization

    • Preparation of syn-Double bent [5]Phenylene: A [CpCo(eth)2]-Mediated Cyclization

    • Preparation of Dehydrobenz[12]annulene 74a: A Stephens-Castro Coupling

    • Hydrogenation of Bis(trimethylsilyl) Bent [4]Phenylene

    • Cyclopropanation of Triangular [4]Phenylene

    • Reaction of Angular [3]Phenylene with TCNE

    • Reaction of Angular [3]Phenylene with [CpCo(eth)2]