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    Chemistry notes

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    1 views2 pages

    Paternò-Büchi Reaction 1

    Uploaded by

    Madhan
    Chemistry notes

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    Download as pdf or txt
    of 2

    Paternò–Büchi reaction

    The Paternò–Büchi reaction, named after Emanuele Paternò and Paternò–Büchi reaction
    George Büchi who established its basic utility and form, is a
    Named after Emanuele Paternò
    photochemical reaction that forms four-membered oxetane rings from
    George Büchi
    an excited carbonyl and reacting with an alkene.[1] [2] [3]
    Reaction type Ring forming
    With substrates benzaldehyde and 2-methyl-2-butene the reaction reaction
    product is a mixture of structural isomers:
    Identifiers
    Organic paterno-buechi-
    Chemistry reaction
    Portal
    RSC ontology RXNO:0000083
    ID

    Here an electronically excited carbonyl group is added to a ground


    state olefin yielding an oxetane.

    Another substrate set is benzaldehyde and furan [4]

    The alternative strategy for the above reaction is called the Transposed Paternò−Büchi reaction.

    The aza-equivalent of the above reactoin is the Aza Paternò−Büchi reaction.

    References
    1. E. Paterno, G. Chieffi (1909). Gazz. Chim. Ital. 39: 341. Missing or empty |title= (help)
    2. G. Büchi; Charles G. Inman; E. S. Lipinsky (1954). "Light-catalyzed Organic Reactions. I. The
    Reaction of Carbonyl Compounds with 2-Methyl-2-butene in the Presence of Ultraviolet Light".
    Journal of the American Chemical Society. 76 (17): 4327–4331. doi:10.1021/ja01646a024 (http
    s://doi.org/10.1021%2Fja01646a024).
    3. Thorsten Bach (1998). "Stereoselective Intermolecular [2 + 2]-Photocycloaddition Reactions
    and Their Application in Synthesis". Synthesis. 1998 (5): 683–703. doi:10.1055/s-1998-2054 (h
    ttps://doi.org/10.1055%2Fs-1998-2054).
    4. Paternò–Büchi Reaction as a Demonstration of Chemical Kinetics and Synthetic
    Photochemistry Using a Light Emitting Diode Apparatus Matthew P. Thompson, Jonathan
    Agger, and Lu Shin Wong Journal of Chemical Education 2015 92 (10), 1716-1720
    doi:10.1021/acs.jchemed.5b00129 (https://doi.org/10.1021%2Facs.jchemed.5b00129)

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    This page was last edited on 24 September 2020, at 06:05 (UTC).

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