Chapter 3.3. Synthetic Utility of the Captodative Effect

  1. Prof. Philippe Renaud1 and
  2. Prof. Mukund P. Sibi2
  1. Lucien Stella and
  2. Jeremy N. Harvey

Published Online: 26 MAR 2008

DOI: 10.1002/9783527618293.ch18

Radicals in Organic Synthesis

Radicals in Organic Synthesis

How to Cite

Stella, L. and Harvey, J. N. (2001) Synthetic Utility of the Captodative Effect, in Radicals in Organic Synthesis (eds P. Renaud and M. P. Sibi), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527618293.ch18

Editor Information

  1. 1

    Universite de Fribourg, Institut de Chimie Organique, Pérolles, CH-1700 Fribourg, Switzerland

  2. 2

    Department of Chemistry, North Dakota State University, Fargo, ND 58105, USA

Publication History

  1. Published Online: 26 MAR 2008
  2. Published Print: 29 MAR 2001

ISBN Information

Print ISBN: 9783527301607

Online ISBN: 9783527618293



  • frontier molecular orbital;
  • alkyloxy;
  • dialkylamino;
  • methylenecyclopropanes;
  • diastereoisomeric mixture


The prelims comprise:

  • Introduction

  • Basic Principles

  • Rearrangement Reactions

  • Selective Oxidation of Captodative Methylene Groups

  • Radical Addition to Captodative Alkenes

  • Radical Reactions of Aromatic Compounds with Captodative Substitution

  • Cycloaddition Reactions Involving Captodative Olefins

  • Conclusions

  • Acknowledgement