Dieckman condensation if two products?

[510586]

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For dieckman condensations, when there are two possible products, is there any order of priority or do you just draw both products like in mixed aldol condensations/ claisens. Because I think sometimes it can react on the other side if it is not symmetric as well using the other o-r group and the other alpha Carbon. Example of this is on 282 of destroyer

 

[DAT Destroyer]

For dieckman condensations, when there are two possible products, is there any order of priority or do you just draw both products like in mixed aldol condensations/ claisens. Because I think sometimes it can react on the other side if it is not symmetric as well using the other o-r group and the other alpha Carbon. Example of this is on 282 of destroyer

This is a good question. If the diester is not symmetrical, indeed 2 possible products could result. The major product would be from the pathway that has the easiest proton to abstract. Look for the alpha proton that has the LEAST amount of steric hindrance. This would likely lead to the major product.

Hope this helps

Dr. Romano

 

[510586]

This is a good question. If the diester is not symmetrical, indeed 2 possible products could result. The major product would be from the pathway that has the easiest proton to abstract. Look for the alpha proton that has the LEAST amount of steric hindrance. This would likely lead to the major product.

Hope this helps

Dr. Romano

Thanks! Does acidity play a role at all or only steric hindrance?

 

[DAT Destroyer]

Thanks! Does acidity play a role at all or only steric hindrance?

It this case acidity plays a very little role. I will try to find some literature references to give you the exact percent of isomeric products. It will likely be around 70:30.

Keep hammering away.

Dr. Romano

 

[510586]

It this case acidity plays a very little role. I will try to find some literature references to give you the exact percent of isomeric products. It will likely be around 70:30.

Keep hammering away.

Dr. Romano

Got it thanks.