Question #e6b23

1 Answer
Jul 29, 2017

Here's one possible sequence.

Explanation:

Step 1. Allylic bromination with N-bromosuccinimide

Step 1

This is also known as the Wohl-Ziegler reaction.

It is a free radical reaction, and bromination occurs preferentially at the secondary carbon because the corresponding intermediate radical is better stabilized.

Step 2. Anti-Markovnikov addition of #"HBr"#

Step 2

This is a free radical addition, not a substitution.

Step 3. Intramolecular Wurtz reaction

Step 3

This method gives good yields of cyclopropanes.