Modeling an Elimination/Migration Reaction:

Overview of this Exercise

We are interested in studying the mechanism for the process of N2 elimination and hydrogen migration in isopropylazide:

The question is whether the reaction occurs via a nitrene intermediate:

or if the elimination and migration are concerted, going through a transition structure such as:

Click on pictures above to see an animation of the transition structure in each case.  Finally, we would like to know how the answer to this question is influenced by the nature of the migrating group.  For instance, what would happen if the hydrogen were replaced by a methyl group?



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