ChemInform Abstract: Pericyclic Reaction Behavior of Cyclopentadienones Toward Acyclic Conjugated Dienes. [3,3]-Sigmatropic Rearrangement and Double Diels—Alder Reactions of the endo[4 + 2]π Cycloadducts.
✍ Scribed by T. JIKYO; M. ETO; K. HARANO
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 36 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Pericyclic Reaction Behavior of Cyclopentadienones Toward Acyclic Conjugated Dienes. [3,3]-Sigmatropic Rearrangement and Double Diels-Alder Reactions of the endo[4 + 2]π Cycloadducts.
-The Diels-Alder reaction of cyclopentadienone (I) with acyclic conjugated dienes (II) leads to the expected endo-products (III) which undergo on heating either a [3,3]-sigmatropic rearrangement to the bicyclic products (IV) or a decarbonylation to give the double Diels-Alder adducts (VI) depending on the reaction temperature. This sequential pericyclic reaction behavior is discussed on the basis of X-ray analysis and molecular orbital calculation data. -(JIKYO, T.;