A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines

Naoya Ohtsuka, Moriaki Okuno, Yujiro Hoshino, Kiyoshi Honda

    抄録

    A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.

    本文言語英語
    ページ(範囲)9046-9054
    ページ数9
    ジャーナルOrganic and Biomolecular Chemistry
    14
    38
    DOI
    ジャーナル掲載日出版済み - 2016

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    Hydroxamic Acids
    Isocyanates
    Carbon Dioxide
    Amines
    Fatty Acids
    Hot Temperature

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    これを引用

    A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines. / Ohtsuka, Naoya; Okuno, Moriaki; Hoshino, Yujiro; Honda, Kiyoshi.

    :: Organic and Biomolecular Chemistry, 巻 14, 番号 38, 2016, p. 9046-9054.

    研究成果: ジャーナルへの寄稿記事

    Ohtsuka, Naoya; Okuno, Moriaki; Hoshino, Yujiro; Honda, Kiyoshi / A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines.

    :: Organic and Biomolecular Chemistry, 巻 14, 番号 38, 2016, p. 9046-9054.

    研究成果: ジャーナルへの寄稿記事

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    AU - Okuno,Moriaki

    AU - Hoshino,Yujiro

    AU - Honda,Kiyoshi

    PY - 2016

    Y1 - 2016

    N2 - A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.

    AB - A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.

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    T2 - Organic and Biomolecular Chemistry

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