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dc.contributor.authorWalton, John Christopher
dc.identifier.citationWalton , J C 2016 , ' Functionalised oximes : emergent precursors for carbon-, nitrogen- and oxygen-centred radicals ' , Molecules , vol. 21 , no. 1 , 63 .
dc.identifier.otherPURE: 240165019
dc.identifier.otherPURE UUID: 39542552-6b1a-4c52-810e-393c88db188e
dc.identifier.otherScopus: 85000470614
dc.identifier.otherWOS: 000369486800036
dc.descriptionThe author thanks EaStCHEM for financial support.en
dc.description.abstractOxime derivatives are easily made, are non-hazardous and have long shelf lives. They contain weak N–O bonds that undergo homolytic scission, on appropriate thermal or photochemical stimulus, to initially release a pair of N- and O-centred radicals. This article reviews the use of these precursors for studying the structures, reactions and kinetics of the released radicals. Two classes have been exploited for radical generation; one comprises carbonyl oximes, principally oxime esters and amides, and the second comprises oxime ethers. Both classes release an iminyl radical together with an equal amount of a second oxygen-centred radical. The O-centred radicals derived from carbonyl oximes decarboxylate giving access to a variety of carbon-centred and nitrogen-centred species. Methods developed for homolytically dissociating the oxime derivatives include UV irradiation, conventional thermal and microwave heating. Photoredox catalytic methods succeed well with specially functionalised oximes and this aspect is also reviewed. Attention is also drawn to the key contributions made by EPR spectroscopy, aided by DFT computations, in elucidating the structures and dynamics of the transient intermediates.
dc.rights© 2016 by the author; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (
dc.subjectOxime estersen
dc.subjectOxime ethersen
dc.subjectFree radicalsen
dc.subjectOrganic synthesisen
dc.subjectPhotochemical reactionsen
dc.subjectEPR spectroscopyen
dc.subjectPhotoredox catalysisen
dc.subjectQD Chemistryen
dc.titleFunctionalised oximes : emergent precursors for carbon-, nitrogen- and oxygen-centred radicalsen
dc.typeJournal itemen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.description.statusPeer revieweden

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