Carbenes and Cyclopropation

Cyclopropanation is the general name for a series of reactions that all produce very similar products by different mechanisms. You may be responsible for one or more of these reactions on your exam, so let’s get into them.

Concept: Reaction with chloroform (CHCl3) and tert-butoxide.

4m

Concept: Reaction with diazomethane and light or heat.

4m

You should not be responsible for the full mechanism of Simmons-Smith, but you should know what the reagents are, and be able to predict that it is a form of cyclopropanation.