The Over-Riding Role of Autocatalysis in Allylic Oxidation

Peter J. Miedziak, Samuel Pattisson, Jennifer K. Edwards, Brian Tarbit, Stuart H. Taylor, Graham J. Hutchings*

*Awdur cyfatebol y gwaith hwn

    Allbwn ymchwil: Cyfraniad at gyfnodolynErthygladolygiad gan gymheiriaid

    3 Wedi eu Llwytho i Lawr (Pure)

    Crynodeb

    In this paper we aim to highlight the need to consider the possible role of autocatalysis in oxidation reactions when using molecular oxygen as the terminal oxidant. Oxygen in its ground state is a diradical, and depending on the reaction conditions, it can initiate oxidation through radical pathways through mechanisms which do not require the presence of a catalyst. Consequently, we contrast the oxidation of benzyl alcohol with oxidation of α-pinene. For benzyl alcohol oxidation the initial reaction is the oxidative dehydrogenation to form benzaldehyde, a non-radical process; but the subsequent over-oxidation to benzoic acid is a radical process. In this case the role of the autocatalysed reaction can be minimised. With α-pinene, the oxidation reaction is via radical pathways and now the autocatalysed reaction can be dominant and, indeed, can be the preferred pathway for the formation of high yields of the desired verbenone product. 

    Iaith wreiddiolSaesneg
    Tudalennau (o-i)1003-1008
    Nifer y tudalennau6
    CyfnodolynCatalysis Letters
    Cyfrol152
    Rhif cyhoeddi4
    Dynodwyr Gwrthrych Digidol (DOIs)
    StatwsCyhoeddwyd - 11 Meh 2021

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