Rearrangements

The direction of rearrangement depends on the nucleophile

The important difference between the following two reactions is the nucleophile used in the reaction. Both reactions go through a very similar aziridinium intermediates, so the difference must be due to the regioselectivity with which the three-membered ring opens in each case. CLICK the nucleophiles below to view each 3D animation respectively.

 

 

 

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