Diels Alder Rxn

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I have a quick question regarding the diels alder reaction. When does the diels alder reaction formulate a trans product? I've been associating the reaction with a cis product most of the time but I came across a bc question where the product was actually trans? Thanks!

 

[teefdocta]

I have a quick question regarding the diels alder reaction. When does the diels alder reaction formulate a trans product? I've been associating the reaction with a cis product most of the time but I came across a bc question where the product was actually trans? Thanks!

Whenever the added Alkene has a trans-configuration then the product will yield a trans product 🙂

 

[DAT Destroyer]

I have a quick question regarding the diels alder reaction. When does the diels alder reaction formulate a trans product? I've been associating the reaction with a cis product most of the time but I came across a bc question where the product was actually trans? Thanks!

The Diels Alder reaction is stereospecific. I have done this reaction for over 30 years. This reaction has been studied extensively. If the dienophile has groups trans......they STAY trans in the final product.....Diels Alder Adduct.

For example, if 1,3-cyclopentadiene reacts with a dienophile having 2 CHO groups trans......the final product would RETAIN this sterochemical relationship. Consult a book written by a PhD Organic Chemist. Klein and McMurray have great Diels Alder examples.

Hope this helps.

Dr. Romano

 

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Thank you!