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  • Organic Chemistry  (3)
  • 1995-1999  (3)
  • 1
    Electronic Resource
    Electronic Resource
    Reactions of 3,5-Diaryl-1,2-dithiolium Salts and 3,5-Diaryl-1,2,4-dithiazolium Salts with Metal Cyclopentadienides (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 221-228 
    Details
    ISSN: 0947-3440
    Keywords: 3,5-Diaryl-1,2-dithiolium salts ; 3,5-Diaryl-1,2,4-dithiazolium salts ; Metal cyclopentadienides ; 3,7-Dithiatricyclo[4.4.0.02,8]deca-4,9-diene ; 3,5-Dithiatricyclo[4.2.2.02,6]deca-7,9-diene ; 3,7-Dithia-5-azatricyclo[4.4.0.02,8]deca-4,9-diene ; Diels-Alder reactions ; Nitrogen heterocycles ; Sulfur heterocycles ; Polycycles ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of the 3,5-diaryl-1,2-dithiolium salts 2 with the metal cyclopentadienides 4 and 9 leads to the formation of the tricyclic compounds 6 and 10 via a ring-opened intermediate, which undergoes an intramolecular Diels-Alder cyclization. Compounds 6 and 10 rearrange by treatment with boron trifluoride-diethyl ether to the isomeric compounds 7 and 11. The structures 6f and 7f were confirmed by X-ray analysis. Condensation of the 3,5-diaryl-1,2,4-dithiazolium salts 3 with the metal cyclopentadienides 4 affords the tricyclic compounds 12, which do not rearrange by Lewis acid catalysis.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970133
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  • 2
    Electronic Resource
    Electronic Resource
    Positional and Facial Selectivity in Diels-Alder Reactions of (-)-(aS,7S)-Colchicine: Synthesis of Novel Analogues of the Alkaloid (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 851-857 
    Details
    ISSN: 0947-3440
    Keywords: Colchicine, diene properties of ; Positional selectivity ; Stabilized exciplex through hydrogen bonding ; π-Facial diastereoselectivity ; Photooxygenation ; Solvent effects ; Cycloadditions ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Positional and facial selectivity in Diels-Alder reactions of several hetero- and carbodienophiles with (-)-(aS,7S)-colchicine (1) has been examined. In all cases, cycloaddition occurred with high positional selectivity at the 8,12-positions of the alkaloid and preferentially from the diene face syn to the allylic substituent at the stereogenic center C-7. The observed high π-facial diastereoselectivity is independent of the polarity of the solvent used and is therefore probably a consequence of steric factors. The structures of the Diels Alder-adducts of 1 with singlet oxygen, N-phenyl-1,2,4-triazolinedione (PTAD) and trans-cyclooctene, 4,5, and 15, respectively, were assigned on the basis of spectral data and verified by X-ray crystallography.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970510
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  • 3
    Electronic Resource
    Electronic Resource
    A Novel Cycloocta[d]-/Barreleno[d]pyridazine RearrangementDedicated to Prof. Dr. Dr. h.c. F. Eiden on the occasion of his 70th birthday. (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 661-666 
    Details
    ISSN: 0947-3440
    Keywords: Cyclooctatetraene-bicyclooctatriene valence tautomerism ; [4+2] Cycloadditions, inverse ; Cycloocta[d]pyridazine ⇛ barreleno[d]pyridazine rearrangement ; [1, 3]-Carbon migration ; Catalysis, 1,3-tautomerization with 2-hydroxypyridine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: As part of the valence tautomeric system cyclooctatetraene (2) bicyclo[4.2.0]octa-2,4,7-triene (3), the monocyclic polyene (2) reacts as a dienophile with the diazadiene 3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine (1) to form after N2-elimination two products: The 1 : 1-adduct 6, a cycloocta[d]pyridazine, and the tetracyclic bis-Diels-Alder cycloadduct 9. Depending on solvent polarity and temperature, compound 6 displays interesting novel rearrangements. On refluxing in nonpolar solvents like toluene, compound 6 yields the barreleno[d]pyridazine 13 in high yield. Compound 13 can be oxidized with 4-phenyltriazolinedione 14 to the barreleno[d]pyridazine 15. When the more polar nitromethane is used as a solvent, heating of 6 at 90° 2°C surprisingly leads to the dihydrocycloocta[d]pyridazine 18 in a multistep reaction including proton-shift tautomerism and [1, 5]-sigmatropic rearrangement. The structures of the compounds 15 and 18 were assigned by the spectral data and verified by X-ray crystallography.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950493
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