'diels alder' like reaction with nonconjugated dienes

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Discussion Overview

The discussion explores whether a reaction similar to the Diels-Alder reaction can occur with non-conjugated dienes, focusing on the necessary geometric configuration for electron transfer. The conversation includes considerations of both synchronous and non-synchronous mechanisms.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant questions if a Diels-Alder-like reaction can occur with non-conjugated dienes, asking for clarification on the geometric configuration required.
  • Another participant suggests that while the proposed conformation may be implausible due to steric hindrance, non-synchronous mechanisms involving radicals could be a more feasible pathway for such reactions.
  • A third participant affirms the legitimacy of the reaction depicted in the provided example.
  • A fourth participant agrees, citing published examples of similar reactions.

Areas of Agreement / Disagreement

While some participants agree that such reactions can occur, there is a lack of consensus on the feasibility of the specific geometric configuration and the mechanisms involved.

Contextual Notes

Participants express uncertainty regarding the plausibility of the conformation due to steric factors and the specifics of the reaction mechanism, particularly the distinction between synchronous and non-synchronous pathways.

Galap
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Can a reaction like the diels alder reaction occur if the diene is not conjugated, but can have the proper geometric configuration for the same electron transfer?

http://i.imgur.com/sFhLg.jpg

Image of example.

If my question is unclear, I can clarify further if necessary.
 
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I think so, but note that in your example there are two hydrogens pointing towards each other which makes the relevant conformation implausible.
On the other hand, if I remember correctly, Diels Alder like reactions may also happen non-synchronously via a mechanism involving radicals, maybe that's more plausible in that case.
 
Yes, the reaction you have on the paper is legitimate.
 
I agree. I have seen such examples published.
 

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