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New reactions and reactive intermediates in the pyrolysis of cyclic phosphonium ylides
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dc.contributor.author | Aitken, R Alan | |
dc.contributor.author | Bjornstad, Vidar | |
dc.contributor.author | Massil, Tracy | |
dc.contributor.author | Skramstad, Jan | |
dc.contributor.author | Young, Robert J. | |
dc.date.accessioned | 2017-09-11T10:30:12Z | |
dc.date.available | 2017-09-11T10:30:12Z | |
dc.date.issued | 2017-08-31 | |
dc.identifier.citation | Aitken , 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.p010.208 | en |
dc.identifier.issn | 1551-7004 | |
dc.identifier.other | PURE: 250439696 | |
dc.identifier.other | PURE UUID: ded8624d-785f-4cb6-9756-5fe45b45bc67 | |
dc.identifier.other | Scopus: 85049183426 | |
dc.identifier.other | ORCID: /0000-0001-6959-5311/work/36661751 | |
dc.identifier.other | WOS: 000451587700001 | |
dc.identifier.uri | https://hdl.handle.net/10023/11640 | |
dc.description | The 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.abstract | Pyrolysis, 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.extent | 9 | |
dc.language.iso | eng | |
dc.relation.ispartof | ARKIVOC | en |
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.subject | Cyclic ylides | en |
dc.subject | Pyrolysis | en |
dc.subject | Phosphoranes | en |
dc.subject | Reactive intermediates | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | New reactions and reactive intermediates in the pyrolysis of cyclic phosphonium ylides | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.24820/ark.5550190.p010.208 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2017-08-31 |
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