Standard Article

Formation of Carbon-Hetero Atom Bonds by Free Radical Chain Additions to Carbon-Carbon Multiple Bonds

  1. F. W. Stacey,
  2. J. F. Harris Jr.

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or013.04

Organic Reactions

Organic Reactions

How to Cite

Stacey, F. W. and Harris, J. F. 2011. Formation of Carbon-Hetero Atom Bonds by Free Radical Chain Additions to Carbon-Carbon Multiple Bonds. Organic Reactions. 13:4:150–376.

Author Information

  1. E. I. du Pont de Nemours and Company, Inc., Central Research Department

Publication History

  1. Published Online: 15 MAR 2011

Abstract

Free-radical chain addition to carbon-carbon multiple bonds to form carbon-hetero atom bonds is an important synthetic method of wide scope. Carbon-halogen, carbon-sulfur, carbon-silicon, carbon-germanium, carbon-phosphorus, and carbon-nitrogen bonds have been formed by this method, In this chapter, the mechanism, scope, limitations, and experimental conditions are treated for the addition reactions that lead to the formation of the six types of carbon-hetero atom bonds mentioned above. Since the direction of addition of free radicals to carbon-carbon multiple bonds is common to all classes reviewed here, it is briefly explained.

Keywords:

  • carbon-hetero bonds;
  • free radical chain;
  • additions;
  • multiple bonds;
  • hydrohalogenation;
  • carbon-sulfur bonds;
  • silanes;
  • germanes;
  • olefins;
  • phosphorus-carbon bonds;
  • carbon-nitrogen bonds;
  • experimental procedures