1
$\begingroup$

am having trouble making sense of products of diels alder reaction. Like I understand the stereochemistry and everything but what I am confused about is how come textbooks don’t give a variety of products that is possible in a diels alder reaction. Like, I know that pericyclic reaction is all about the symmetry of lobes of dienphile and diene. That is exactly how the difference between antafacial and superfacial come in, in that in antarafacial since the lobes are not in symmetry, you have to twist the molecule to get symmetry. So in the same sense, I have realized that when u do diels alder reaction depending on the way you organize the lobes of the diene and dienophile you can get so many possible products. However textbooks don’t really mention this phenomenon at all. I have shown what I mean by different lobe symmetry in the picture below. Can anyone tell me what is going on or am I overthinking this or what?enter image description here

$\endgroup$
  • 1
    $\begingroup$ You are best served by looking up in a textbook "regioselectivity" and "stereoselectivity" of "Diels-Alder reactions". Any good organic chem textbook (e.g. Clayden) will have a section on it. $\endgroup$ – orthocresol Mar 23 '17 at 22:11
  • $\begingroup$ I think the answer to the first question is that it does not serve beginning students to know the great variety of Diels-Alder reactions. $\endgroup$ – Zhe Mar 23 '17 at 22:33
  • $\begingroup$ Okay. Orthocresol, yes, sometimes, when there are certain substituents that make preference for one product over another, this question of lobe symmetry and diferent products does not matter. But when I was thinking of this question, I was thinking in terms of those substituents that don't really make this preference. $\endgroup$ – TLo Mar 23 '17 at 22:53
  • $\begingroup$ The diene would be too strained to undergo an antarafacial reaction. Was that your question? $\endgroup$ – Jan Mar 28 '17 at 16:14

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.