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dc.contributor.authorSCANLAN, EOINen
dc.date.accessioned2014-11-24T16:41:43Z
dc.date.available2014-11-24T16:41:43Z
dc.date.issued2004en
dc.date.submitted2004en
dc.identifier.citationScanlan, Eoin M.; Slawin, Alexandra M. Z.; Walton, John C., Preparation of b- and g-lactams from carbamoyl radicals derived from oxime oxalate amides., Organic & Biomolecular Chemistry, 2, 2004, 716, 724en
dc.identifier.otherYen
dc.identifier.urihttp://hdl.handle.net/2262/72177
dc.descriptionPUBLISHEDen
dc.description.abstractA general synthetic route to oxime oxalate amides was developed and applied to the preparation of molecules incorporating N -benzyl- N -alkenyl amides linked with acetone oxime or benzaldoxime units. In addition, 2-substituted-thiazolidine-4-carboxylic acid methyl ester amides of oxalyl benzaldoxime were also prepared. It was shown by EPR spectroscopy that the oxalyl benzaldoxime amides dissociated to produce benziminyl and carbamoyl (aminoacyl) radicals when photolysed with 4-methoxyacetophenone as a photosensitizer. Carbamoyl radicals derived from N -alk-3-enyl oxime oxalate amides underwent ring closure to a ff ord pyrrolidin-2-ones. The analogous N -alk-2- enyl precursors a ff orded azetidin-2-ones. Reactions of the cyclohexenyl and cinnamyl oxime oxalate amides a ff orded a bicyclic β -lactam and a 3-benzyl-substituted β -lactam respectively. Interestingly, both products were isolated as hydroxylated compounds. A thiazolidine-derived oxime oxalate amide containing an isobutenyl side chain also dissociated with production of the corresponding thiazolidinyl-carbamoyl radical, as shown by EPR spectroscopy. GC-MS evidence indicated that this radical cyclised to a ff ord some of the corresponding penicillin derivativeen
dc.format.extent716en
dc.format.extent724en
dc.language.isoenen
dc.relation.ispartofseriesOrganic & Biomolecular Chemistryen
dc.relation.ispartofseries2en
dc.rightsYen
dc.subjectChemistryen
dc.titlePreparation of b- and g-lactams from carbamoyl radicals derived from oxime oxalate amides.en
dc.typeJournal Articleen
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/scanlaeen
dc.identifier.rssinternalid50439en
dc.rights.ecaccessrightsopenAccess


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