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

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)9046-9054
    Number of pages9
    JournalOrganic and Biomolecular Chemistry
    Volume14
    Issue number38
    DOIs
    StatePublished - 2016

    Fingerprint

    Hydroxamic Acids
    Isocyanates
    Carbon Dioxide
    Amines
    Fatty Acids
    Hot Temperature

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    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.

    In: Organic and Biomolecular Chemistry, Vol. 14, No. 38, 2016, p. 9046-9054.

    Research output: Contribution to journalArticle

    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.

    In: Organic and Biomolecular Chemistry, Vol. 14, No. 38, 2016, p. 9046-9054.

    Research output: Contribution to journalArticle

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