Diels−Alder Reactions of 1,3-Diphenylisobenzofuran with Ferrocenyl- and (η6-Phenyl)tricarbonylchromium Analogues of Chalcone as Well as Some Other Dienophiles
| Autor: | Štefan Toma, and Ali A. Torabi, Eva Solčániová, Kenneth W. Muir, Graham R. Knox, Monika Prokešová |
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| Rok vydání: | 1996 |
| Předmět: | |
| Zdroj: | The Journal of Organic Chemistry. 61:3392-3397 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo9500850 |
| Popis: | The Diels−Alder reactions of 1,3-diphenylisobenzofuran with acryloylferrocene (1), 4-ferrocenyl-3-buten-2-one (2), cinnamoylferrocene (3), 3-ferrocenyl-1-phenyl-2-propenone (4), chalcone (5), 1-((η6-phenyl)tricarbonylchromio)-3-phenyl-2-propenone (6), 1-phenyl-3-((η6-phenyl)tricarbonylchromio)-2-propenone (7), and (2-nitrovinyl)ferrocene (8) were examined under various conditions. The best results were achieved using SiO2 and a very acidic montmorillonite clay, KSF, as the catalyst, and the reactions were carried out without solvent. Reasonable to good yields of the Diels−Alder (D-A) products were isolated in most cases. X-ray structural studies showed that the adducts 13b and 13h, derived from the (E)-alkenes 2 and 8, have exo-acetyl or -nitro substituents and endo-ferrocenyl groups with respect to the bridging oxygen atom of the 7-oxabicycloheptane ring system. The product 13a from the monosubstituted enone 1 also has an exo-acyl (ferrocenylcarbonyl) group. Aluminum chloride was found to be a good catal... |
| Databáze: | OpenAIRE |
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