9. Pyrroles

  1. John A. Joule1 and
  2. Keith Mills2

Published Online: 6 AUG 2012

DOI: 10.1002/9781118380208.ch9

Heterocyclic Chemistry at a Glance, Second Edition

Heterocyclic Chemistry at a Glance, Second Edition

How to Cite

Joule, J. A. and Mills, K. (2012) Pyrroles, in Heterocyclic Chemistry at a Glance, Second Edition, John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9781118380208.ch9

Author Information

  1. 1

    The School of Chemistry, The University of Manchester, UK

  2. 2

    Independent Consultant, UK

Publication History

  1. Published Online: 6 AUG 2012
  2. Published Print: 4 SEP 2012

ISBN Information

Print ISBN: 9780470971222

Online ISBN: 9781118380208

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Keywords:

  • pyrroles;
  • electrophilic substitution at carbon;
  • pyrroles and electrophilic C-substitution, at α-position;
  • positional selectivity/high reactivity, mesomeric to intermediates;
  • Vilsmeier reaction, forming pyrrole aldehydes;
  • electron-withdrawing groups on nitrogen/carbon;
  • modifying electrophilic attack regioselectivity;
  • N-deprotonation and N-metallated pyrroles;
  • side-chain substituent reactivity;
  • heme/chlorophyll biology in pyrrole chemistry

Summary

This chapter contains sections titled:

  • Electrophilic substitution at carbon

  • N-Deprotonation and N-metallated pyrroles

  • C-Metallated pyrroles

  • Palladium(0)-catalysed reactions

  • Oxidation and reduction

  • Pericyclic reactions

  • Reactivity of side-chain substituents

  • The ‘pigments of life’

  • Ring synthesis – disconnections

  • Synthesis of pyrroles from 1,4-dicarbonyl compounds

  • Synthesis of pyrroles from α-amino-ketones

  • Synthesis of pyrroles using isocyanides

  • Exercises