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  • 1
    Electronic Resource
    Electronic Resource
    On the Behavior of 5,8-Bis(trimethylsilyl)cycloocta-1,3,6-triene in Cycloaddition Reactions and Subsequent Chemistry (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1041-1050 
    Details
    ISSN: 1434-193X
    Keywords: Phosphaalkynes ; Cycloadditions ; Polycycles ; Cage compounds ; λ3-Phosphinines ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Phosphaalkynes 2 and electron-deficient alkynes 11 readily react in a [4 + 2] cycloaddition process with 5,8-bis(trimethylsilyl)cycloocta-1,3,6-triene (8) in its bicyclic form 10 to furnish regioselectively the tricyclodecadienes 12 and 13, respectively. The phosphorus-containing compounds 12 exhibit structural features which make them suitable for homo-Diels-Alder reactions with electron-deficient acetylenes. A single crystal structure analysis of the homo-Diels-Alder adduct 14b confirmed the structure and relative configuration of the phophatricyclodecadienes 12. In solution the tricyclodecadienes 13 are prone to facile cycloreversion yielding the phthalic esters 15 and the cyclobutene 16. The latter is rapidly converted into the corresponding 1,3-butadiene 18, which can be trapped in a Diels-Alder/phospha-ene/Diels-Alder tandem reaction sequence by phosphaalkyne 2a. The phosphatricyclodecadiene 12 is thermally more stable; loss of cyclobutene 16 only occurs under FVP conditions to afford the λ3-phosphinine 22.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Synthese von Metallkomplexen mit Bis(phenalenyl)imin-Liganden (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 1119-1124 
    Details
    ISSN: 0170-2041
    Keywords: Phenalenones, hydroxy- ; Bis(phenalenyl)imine ligands ; Acenaphthenequinones ; Roesleria hypogea, pigments of ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Metal Complexes with Bis(phenalenyl)imine LigandsSynthesis of model pigments and their metal chelates with Zn, Co, Ni, and Mn (26a-d) are described. The former are obtained from 2,4-dihydro-4,9-dihydroxy-1,2,4-phenalenethione (14b) by connecting two molecules in a ninhydrin-like reaction with nitrogen to the ligand 8. These models confirm the structure of the zinc complex 2 isolated from the ascomyces Roesleria hypogea. Isolation of the rearranged ester 18 proves this compound to be an intermediate in the mechanism of the degradation process of phenalenetriones 14 to acenaphthoquinones 16.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001203
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    Paper (German National Licenses)
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