Cyclization to the Carbonyl Group

In the following displays carbon is dark gray, hydrogen is cyan, oxygen is red and nitrogen is blue. In the model on the left, the nitrogen is oriented to bond to the carbonyl group of the unsaturated ester. On the right, the nitrogen is oriented to bond to the beta-carbon of the conjugated ester (Michael addition). These represent the best possible bonding orientations, and the N-C distances are similar. Note that the orbital alignment on the right is poorer than that on the left.

 

 


End of this supplementary topic