Correlations between Carbon-13 Nuclear Magnetic Resonance Chemical Shifts and Reactivities of Siloxybutadienes and Siloxyazabutadienes in the Diels-Alder Reaction with Dimethyl Acetylenedicar-boxylate

Jun Etsu Igarashi, Yoshinari Kawakami, Toshio Kinoshita, Sunao Furukawa

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)

    Abstract

    In the reaction of silylated butadiene derivatives (1) with dimethyl acetylenedicarboxylate (DMAD), it is proposed that the reactivities of the dienes can be predicted from the carbon-13 nuclear magnetic resonance chemical shifts of the terminal methylene carbons (£13C-4) of the dienes based on the following linear relationships, a) total electron densities against d13C-4; b) In k against l/[£LuMO(DMAD)-£HOMo<die„e)]; c) In k against <513C-4. The total electron densities and energy levels of highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) of the dienes were calculated by the modified neglect of diatomic overlap (MNDO) method.

    Original languageEnglish
    Pages (from-to)1832-1835
    Number of pages4
    JournalChemical and Pharmaceutical Bulletin
    Volume38
    Issue number7
    DOIs
    Publication statusPublished - 1990

    All Science Journal Classification (ASJC) codes

    • Chemistry(all)
    • Drug Discovery

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