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New chemistry of chiral 1,3-dioxolan-4-ones
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dc.contributor.author | Aitken, R Alan | |
dc.contributor.author | Power, Lynn A. | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.date.accessioned | 2023-05-02T11:30:13Z | |
dc.date.available | 2023-05-02T11:30:13Z | |
dc.date.issued | 2023-05-01 | |
dc.identifier | 285036226 | |
dc.identifier | 91ab86a9-71df-43ca-ada2-05bb0b072d48 | |
dc.identifier | 85159171024 | |
dc.identifier.citation | Aitken , R A , Power , L A & Slawin , A M Z 2023 , ' New chemistry of chiral 1,3-dioxolan-4-ones ' , Molecules , vol. 28 , no. 9 , 3845 . https://doi.org/10.3390/molecules28093845 | en |
dc.identifier.issn | 1420-3049 | |
dc.identifier.other | ORCID: /0000-0001-6959-5311/work/134491268 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/134491310 | |
dc.identifier.uri | https://hdl.handle.net/10023/27483 | |
dc.description | Funding: Authors thank the School of Chemistry for a studentship to L. A. P. | en |
dc.description.abstract | (2S,5S)-5-Phenyl-2-t-butyl-1,3-dioxolan-4-one, readily derived from mandelic acid, undergoes Michael addition to butenolide and 4-methoxy-β-nitrostyrene with the absolute configuration of the products confirmed by X-ray diffraction in each case. In the former case thermal fragmentation gives the phenyl ketone thus illustrating use of the dioxolanone as a chiral benzoyl anion equivalent. The Diels–Alder cycloaddition chemistry of (2S)-5-methylene-2-t-butyl-1,3-dioxolan-4-one, derived from lactic acid, has been further examined with X-ray structures of four adducts determined. In one case thermal fragmentation of the adduct gives a chiral epoxy ketone resulting from the dioxolanone acting as a chiral ketene equivalent, while in others the products give insight into the mechanism of the dioxolanone fragmentation process. | |
dc.format.extent | 18 | |
dc.format.extent | 3602660 | |
dc.language.iso | eng | |
dc.relation.ispartof | Molecules | en |
dc.subject | Dioxolanones | en |
dc.subject | Michael addition | en |
dc.subject | Diels–Alder reaction | en |
dc.subject | Flash vacuum pyrolysis | en |
dc.subject | X-ray structure | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | MCC | en |
dc.subject.lcc | QD | en |
dc.title | New chemistry of chiral 1,3-dioxolan-4-ones | 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/10.3390/molecules28093845 | |
dc.description.status | Peer reviewed | en |
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