The palladium-catalyzed intramolecular cyclization of alkadienyl-substituted 1,3-diketones
| Autor: | Peter W. Jolly, Cornelia Wirtz, Carl Krüger, G. Hopp, Richard Mynott, Richard Goddard |
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| Rok vydání: | 1995 |
| Předmět: |
Acetylacetone
Organic Chemistry Intramolecular cyclization chemistry.chemical_element Cyclohexanone Crystal structure Biochemistry Medicinal chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Materials Chemistry Organic chemistry Physical and Theoretical Chemistry Enone Palladium |
| Zdroj: | Journal of Organometallic Chemistry. 486:163-170 |
| ISSN: | 0022-328X |
| Popis: | Hydroxydeca-3,7,9-triene-2-one (prepared by metallation of acetylacetone followed by treatment with 1-bromopenta-2,4-diene) undergoes intramolecular cyclization in the presence of a [Pd(iPr2PC2H4PiPr2)] catalyst to give a mixture of cyclohexanone and cycloheptenone derivatives. The cyclohexanone 2-(1-hydroxyethyliden)-3-vinylcyclohexanone isomerizes in the presence of palladium to give the palladium-alkene complex (η 2 -2- acetyl -3- ethylcyclohex -2- enone ) Pd ( i Pr 2 PC 2 H 4 P i Pr 2 ) whose crystal structure has been established by X-ray diffraction. A related cyclization reaction involving the disubstituted 1,3-diketone 9-hydroxy-1,3,7,12,14-pentaene-7-one leads to the formation of a mixture of spiro compounds (mainly 5,11-divinyl-spiro[5.5]undeca-1,7-dione) whose structures have been elucidated with the help of 1H- and 13C-NMR spectroscopies using 2D-NMR techniques. |
| Databáze: | OpenAIRE |
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