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 in | Chemical & pharmaceutical bulletin Vol. 45; no. 12; p. 1961 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Tokyo
Japan Science and Technology Agency
01.12.1997
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Online Access | Get full text |
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Summary: | 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. |
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ISSN: | 0009-2363 1347-5223 |