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  • 1
    Electronic Resource
    Electronic Resource
    Carbon-Carbon Bond Cleavage of the [2.2]Paracyclophane Radical Cation Generated by Electron Transfer Oxidation with Cerium(IV) Ammonium Nitrate (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 875-879 
    Details
    ISSN: 0009-2940
    Keywords: [2.2]Paracyclophanes ; Electron transfer reactions ; Radicals ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Single electron transfer (SET) oxidation of [2.2]paracyclophane (1) with cerium ammonium nitrate (CAN) produces the corresponding radical cation (1+.), which undergoes cleavage of the carbon-carbon bond of the ethano bridge to generate the double-benzylic radical cation 2+. Trapping of this intermediate by oxygen and nucleophiles gives rise to aldehydes 3, while a second oxidation and subsequent nucleophilic trapping affords nitrates 4. This facile cleavage of the carbon-carbon bond is explained by alignment of the latter with the π systems in the rigid structure of [2.2]paracyclophane, which enables charge delocalization across both benzene rings. When the reaction is carried out in methanol, aromatic substitution takes also place as a minor reaction pathway, which is responsible for the formation of the polyfunctionalized cyclophane 5d.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270514
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Isolation and Synthesis of N-(2-Methyl-3-oxodec-8-enoyl)-2-pyrroline and 2-(Hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]1,3-oxazine - Two New Fungal Metabolites with in vivo Anti-Juvenile-Hormone and Insecticidal Activity (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 221-226 
    Details
    ISSN: 1434-193X
    Keywords: β-Ketoamide ; Penicillium brevicompactum ; Fungal metabolites ; Anti-JH activity ; Insecticides ; Fungicide ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Two new natural products, N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (2) and 2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine (3), have been isolated from Penicillium brevicompactum Dierckx. Compound 2 has shown an important in vivo anti-juvenile-hormone (anti-JH) activity while compound 3 has exhibited insecticidal activity against Oncopeltus fasciatus Dallas. Both products have been synthesized starting from 1,4-hexadiene, by means of a sequence of reactions which includes the preparation of 6-octenoic acid and its transformation into the corresponding acid chloride, in order to acylate Meldrum's acid. Subsequent aminolysis with pyrrolidine, followed by methylation at the activated position of the β-oxo amide with iodomethane, introduction of a methoxy group at the pyrrolidine ring by anodic oxidation and final elimination of methanol on SiO2 led to 2 and 3. The fact that both metabolites can be prepared by the same sequence indicates that they must be biogenetically related. Based on structural similarities, compounds 2 and 3 are also closely related to the recently discovered brevioxime (1).
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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