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Unexpected Cleavage of 2-Azido-2-(hydroxymethyl)oxetanes: Conformation Determines Reaction Pathway?

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2010, 75, 22, 7565-7572
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    Unexpected Cleavage of 2-Azido-2-(hydroxymethyl)oxetanes: Conformation Determines Reaction Pathway?
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    Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States
    *Corresponding author. [email protected] Phone: 860-486-3460. Fax: 860-486-2981.
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2010, 75, 22, 7565–7572
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    https://doi.org/10.1021/jo101328c
    Published October 18, 2010
    Copyright © 2010 American Chemical Society
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    Abstract

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    An unanticipated cleavage of 2-azido-2-(hydroxymethyl)oxetanes is reported. In attempts to oxidize the title oxetanyl alcohols to the corresponding carboxylic acids with RuO4, cleaved nitriles were formed as the sole isolable products, while a closely related tetrahydrofuran gave solely the expected carboxylic acid. Quantum chemical calculations suggest that the divergent outcomes are governed by conformational differences in the azidoalcohols.

    Copyright © 2010 American Chemical Society

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    General experimental methods and procedures, spectroscopy data and 1H and 13C NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    This article is cited by 12 publications.

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    2. Jeong Min Lee, Dae Young Bae, Jin Yong Park, Hwi Yul Jo, Eunsung Lee, Young Ho Rhee, Jaiwook Park. Concurrent Formation of N–H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C–C Bond Cleavage of β-Hydroxy Azides. Organic Letters 2020, 22 (12) , 4608-4613. https://doi.org/10.1021/acs.orglett.0c01145
    3. Christian A. Malapit and Amy R. Howell . Recent Applications of Oxetanes in the Synthesis of Heterocyclic Compounds. The Journal of Organic Chemistry 2015, 80 (17) , 8489-8495. https://doi.org/10.1021/acs.joc.5b01255
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2010, 75, 22, 7565–7572
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo101328c
    Published October 18, 2010
    Copyright © 2010 American Chemical Society
    Request reuse permissions

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