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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Theoretical Study of Endo Selectivity in the Diels-Alder Reactions between Butadienes and Cyclopropene

Masahiro Imade1, Hajime Hirao, Kiyoyuki Omoto

  • 1Division of Molecular Engineering, Kyoto University, Kyoto 606-8501, Japan.

The Journal of Organic Chemistry
|October 25, 2001
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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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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