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A remarkable cis- and trans-spanning dibenzylidene acetone diphosphine chelating ligand (dbaphos)

Amanda G Jarvis1, Petr E Sehnal, Somia E Bajwa

  • 1Department of Chemistry, University of York, York, YO10 5DD, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 16, 2013
PubMed

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
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A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.