Pericyclic Reaction Behavior of Cyclopentadienones toward Acyclic Conjugated Dienes. [3, 3]-Sigmatropic Rearrangement and Double Diels-Alder Reactions of the endo[4+2][pi] Cycloadducts

Cycloaddition of 2, 5-disubstituted-3, 4-diphenylcyclopentadienone with acyclic conjugated dienes gave the endo [4+2]π cycloadducts, which then underwent [3, 3]-sigmatropic rearrangement to give the corresponding endo [2+4]π cycloadduct on heating at 110°C. Pyrolysis of the endo [4+2]π cycloadducts...

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Published inChemical & pharmaceutical bulletin Vol. 45; no. 12; p. 1961
Main Authors JIKYO, Tamaki, ETO, Masashi, HARANO, Kazunobu
Format Journal Article
LanguageEnglish
Published Tokyo Japan Science and Technology Agency 01.12.1997
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Abstract Cycloaddition of 2, 5-disubstituted-3, 4-diphenylcyclopentadienone with acyclic conjugated dienes gave the endo [4+2]π cycloadducts, which then underwent [3, 3]-sigmatropic rearrangement to give the corresponding endo [2+4]π cycloadduct on heating at 110°C. Pyrolysis of the endo [4+2]π cycloadducts at 170°C resulted in decarbonylation to give the double Diels-Alder adduct. The sequential pericyclic reaction behavior is discussed on the basis of X-ray diffraction analyses and molecular orbital calculation data.
AbstractList Cycloaddition of 2, 5-disubstituted-3, 4-diphenylcyclopentadienone with acyclic conjugated dienes gave the endo [4+2]π cycloadducts, which then underwent [3, 3]-sigmatropic rearrangement to give the corresponding endo [2+4]π cycloadduct on heating at 110°C. Pyrolysis of the endo [4+2]π cycloadducts at 170°C resulted in decarbonylation to give the double Diels-Alder adduct. The sequential pericyclic reaction behavior is discussed on the basis of X-ray diffraction analyses and molecular orbital calculation data.
Author HARANO, Kazunobu
ETO, Masashi
JIKYO, Tamaki
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Title Pericyclic Reaction Behavior of Cyclopentadienones toward Acyclic Conjugated Dienes. [3, 3]-Sigmatropic Rearrangement and Double Diels-Alder Reactions of the endo[4+2][pi] Cycloadducts
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