Show simple item record

Files in this item

Thumbnail

Item metadata

dc.contributor.authorAitken, R Alan
dc.contributor.authorBjornstad, Vidar
dc.contributor.authorMassil, Tracy
dc.contributor.authorSkramstad, Jan
dc.contributor.authorYoung, Robert J.
dc.date.accessioned2017-09-11T10:30:12Z
dc.date.available2017-09-11T10:30:12Z
dc.date.issued2017-08-31
dc.identifier.citationAitken , R A , Bjornstad , V , Massil , T , Skramstad , J & Young , R J 2017 , ' New reactions and reactive intermediates in the pyrolysis of cyclic phosphonium ylides ' , ARKIVOC , vol. 2017 , no. iii , pp. 293-301 . https://doi.org/10.24820/ark.5550190.p010.208en
dc.identifier.issn1551-7004
dc.identifier.otherPURE: 250439696
dc.identifier.otherPURE UUID: ded8624d-785f-4cb6-9756-5fe45b45bc67
dc.identifier.otherScopus: 85049183426
dc.identifier.otherORCID: /0000-0001-6959-5311/work/36661751
dc.identifier.otherWOS: 000451587700001
dc.identifier.urihttp://hdl.handle.net/10023/11640
dc.descriptionThe authors are grateful to EPSRC and Glaxo-Wellcome (now GSK) for their support of this work through a CASE Studentship to TM.en
dc.description.abstractPyrolysis, either neat or in diphenyl ether solution, results in the conversion of both 4-triphenylphosphoranylidenetetrahydrofuran-2,3,5-trione and 4-triphenylphosphoranylidenetetrahydrothio-phene-2,3,5-trione into 3,5-bis(triphenylphosphoranylidene)cyclopentane-1,2,4-trione. These reactions involve extrusion of CO2 or COS to give 3-triphenylphosphoranylidenecyclopropane-1,2-dione which further loses CO to give triphenylphosphoranylideneketene. The precise way in which these two reactive phosphorus compounds combine to give the observed product has been examined by chemical and isotopic labelling studies. Cyclotrimerization of triphenylphosphoranylideneketene upon thermolysis in diphenyl ether has also been observed for the first time. The erroneous literature interpretation of the 13C NMR spectrum for triphenylphosphoranylideneketene is corrected.
dc.format.extent9
dc.language.isoeng
dc.relation.ispartofARKIVOCen
dc.rights© ARKAT USA, Inc. 2017. This is an open access article published under a Creative Commons Attribution-NonCommercial 4.0 International licence (CC BY-NC 4.0) - https://creativecommons.org/licenses/by-nc/4.0/en
dc.subjectCyclic ylidesen
dc.subjectPyrolysisen
dc.subjectPhosphoranesen
dc.subjectReactive intermediatesen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleNew reactions and reactive intermediates in the pyrolysis of cyclic phosphonium ylidesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.24820/ark.5550190.p010.208
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-08-31


This item appears in the following Collection(s)

Show simple item record