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Flash vacuum pyrolysis of oxo-stabilised phosphonium ylides containing methoxythiophene and methylthiophene groups
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dc.contributor.author | Aitken, R. Alan | |
dc.contributor.author | Garnett, Alasdair N. | |
dc.date.accessioned | 2019-08-22T23:44:12Z | |
dc.date.available | 2019-08-22T23:44:12Z | |
dc.date.issued | 2018-10-16 | |
dc.identifier | 255453604 | |
dc.identifier | e07bed20-4eb8-4d74-b0a9-48118acd61af | |
dc.identifier | 85053810419 | |
dc.identifier | 000449125700041 | |
dc.identifier.citation | Aitken , 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.2018.08.013 | en |
dc.identifier.issn | 0165-2370 | |
dc.identifier.other | ORCID: /0000-0001-6959-5311/work/47725844 | |
dc.identifier.uri | https://hdl.handle.net/10023/18356 | |
dc.description | We thank EPSRC (UK) for a studentship to ANG. | en |
dc.description.abstract | Ten 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.extent | 10 | |
dc.format.extent | 662750 | |
dc.language.iso | eng | |
dc.relation.ispartof | Journal of analytical and applied pyrolysis | en |
dc.subject | Flash vacuum pyrolysis | en |
dc.subject | Phosphonium ylide | en |
dc.subject | Thienofuran | en |
dc.subject | Benzothiophene | en |
dc.subject | Fluorenothiophene | en |
dc.subject | Radical cyclisation | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Flash vacuum pyrolysis of oxo-stabilised phosphonium ylides containing methoxythiophene and methylthiophene groups | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1016/j.jaap.2018.08.013 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-08-23 |
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