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  The palladium-catalyzed intramolecular cyclization of alkadienyl-substituted 1,3-diketones

Goddard, R., Hopp, G., Jolly, P. W., Krüger, C., Mynott, R., & Wirtz, C. (1995). The palladium-catalyzed intramolecular cyclization of alkadienyl-substituted 1,3-diketones. Journal of Organometallic Chemistry, 486(1-2), 163-170. doi:10.1016/0022-328X(94)05017-6.

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 Creators:
Goddard, R.1, Author              
Hopp, G.2, Author
Jolly, P. W.2, Author              
Krüger, C.1, Author              
Mynott, R.3, Author              
Wirtz, C.3, Author              
Affiliations:
1Service Department Krüger (XRAY), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445624              
2Research Department Jolly, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445580              
3Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              

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Free keywords: Palladium catalysis; Intramolecular cyclization; 1,3-diketones
 Abstract: 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 (η2-2-acetyal-3-ethylcyclohex-2-enone)Pd(iPr2PC2H4PiPr2) 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.

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Language(s): eng - English
 Dates: 1995-01-25
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/0022-328X(94)05017-6
 Degree: -

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Title: Journal of Organometallic Chemistry
  Other : J. Organomet. Chem.
Source Genre: Journal
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Publ. Info: Amsterdam : Elsevier
Pages: - Volume / Issue: 486 (1-2) Sequence Number: - Start / End Page: 163 - 170 Identifier: ISSN: 0022-328X
CoNE: https://pure.mpg.de/cone/journals/resource/954925622228