The over-riding role of autocatalysis in alllylic oxidation

Miedziak, Peter J., Pattisson, Samuel, Edwards, Jennifer K. ORCID: https://orcid.org/0000-0003-4089-2827, Tarbit, Brian, Taylor, Stuart H. ORCID: https://orcid.org/0000-0002-1933-4874 and Hutchings, Graham J. ORCID: https://orcid.org/0000-0001-8885-1560 2022. The over-riding role of autocatalysis in alllylic oxidation. Catalysis Letters 152 , pp. 1003-1008. 10.1007/s10562-021-03707-4

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Abstract

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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Additional Information:	This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made.
Publisher:	Springer
ISSN:	1011-372X
Date of First Compliant Deposit:	16 June 2021
Date of Acceptance:	5 June 2021
Last Modified:	02 May 2023 19:08
URI:	https://orca.cardiff.ac.uk/id/eprint/141934

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