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Silicon-mediated organic synthesis.

L A Paquette

    Science (New York, N.Y.)
    |August 27, 1982
    PubMed
    Summary
    This summary is machine-generated.

    Organic chemists leverage tetracovalent silicon

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    Area of Science:

    • Organic Chemistry
    • Organosilicon Chemistry
    • Synthetic Chemistry

    Background:

    • Tetracovalent silicon exhibits unique chemical properties.
    • Carbon-functional silanes demonstrate exceptional stabilization of carbocations.
    • Silicon's ability to stabilize adjacent carbon-metal bonds is well-established.

    Purpose of the Study:

    • To explore novel synthetic transformations utilizing tetracovalent silicon.
    • To elucidate the mechanisms of silicon-directed electrophilic attacks.
    • To highlight the preparative applications of silicon's chemical properties.

    Main Methods:

    • Investigation of electrophilic attack on various silanes (aryl-, vinyl-, alkynyl-, allyl-).
    • Synthesis and characterization of silicon-containing organometallic compounds.

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  • Analysis of silicon reagent reactivity influenced by Si-O and Si-F bond strengths.

    • Main Results:

    • Electrophilic attack is directed to silicon-substituted carbons or specific allylic positions due to beta-silicon effect.
    • Readily accessible routes to silicon-containing organometallics are demonstrated.
    • The influence of strong silicon-oxygen and silicon-fluorine bonds on reactivity is confirmed.

    Conclusions:

    • Tetracovalent silicon enables diverse and valuable synthetic transformations.
    • Understanding silicon's electronic effects is key to controlling reactivity.
    • Recent advancements showcase imaginative uses of silicon reagents in organic synthesis.