Chapter 23: Aryl Halides

Diels-Alder Reactions of Benzyne

• Benzyne can undergo Diels-Alder reactions leading to the formation of fused ring systems with an aromatic component:

• A milder, more convienient method for the generation of benzyne involves treating 1,2-bromofluorobenzyne with magnesium metal:

• The strained triple bond makes benzyne a good dienophile

© Dr. Ian Hunt, Department of Chemistry, University of Calgary