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dc.contributor.authorAitken, R. Alan
dc.contributor.authorGarnett, Alasdair N.
dc.date.accessioned2019-08-22T23:44:12Z
dc.date.available2019-08-22T23:44:12Z
dc.date.issued2018-10-16
dc.identifier.citationAitken , R A & Garnett , A N 2018 , ' Flash vacuum pyrolysis of oxo-stabilised phosphonium ylides containing methoxythiophene and methylthiophene groups ' , Journal of analytical and applied pyrolysis , vol. 135 , pp. 369-378 . https://doi.org/10.1016/j.jaap.2018.08.013en
dc.identifier.issn0165-2370
dc.identifier.otherPURE: 255453604
dc.identifier.otherPURE UUID: e07bed20-4eb8-4d74-b0a9-48118acd61af
dc.identifier.otherScopus: 85053810419
dc.identifier.otherORCID: /0000-0001-6959-5311/work/47725844
dc.identifier.otherWOS: 000449125700041
dc.identifier.urihttp://hdl.handle.net/10023/18356
dc.descriptionWe thank EPSRC (UK) for a studentship to ANG.en
dc.description.abstractTen new oxo-stabilised phosphonium ylides containing substituted thiophene groups, as well as two deuterium-labelled analogues, are prepared and fully characterised. Upon flash vacuum pyrolysis at 800 °C, the simpler examples undergo extrusion of Ph3PO coupled with domino cyclisation to give thieno[3,2-b]furan and thieno[3,4-b]furan products but the corresponding approach to a thieno[2,3-b]furan fails. One ylide designed to give a thieno[3,4-b]furan instead gives phenylbutadiyne and 2-phenyl-3-vinylthiophene at 725 °C and the mechanism of this unusual process is elucidated by deuterium labelling. Attempts to access more complex heterocyclic products from extended methoxythienyl ylides failed. Two ylides bearing a 3-methyl-2-thienylacryloyl group gave 5-benzylbenzothiophene, 5-(α-methylbenzyl)benzothiophene and fluoreno[3,4-b]thiophene upon FVP at 800 °C and the mechanism was again elucidated by deuterium labelling.
dc.format.extent10
dc.language.isoeng
dc.relation.ispartofJournal of analytical and applied pyrolysisen
dc.rights© 2018 Elsevier B.V. All rights reserved. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.jaap.2018.08.013en
dc.subjectFlash vacuum pyrolysisen
dc.subjectPhosphonium ylideen
dc.subjectThienofuranen
dc.subjectBenzothiopheneen
dc.subjectFluorenothiopheneen
dc.subjectRadical cyclisationen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleFlash vacuum pyrolysis of oxo-stabilised phosphonium ylides containing methoxythiophene and methylthiophene groupsen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1016/j.jaap.2018.08.013
dc.description.statusPeer revieweden
dc.date.embargoedUntil2019-08-23


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