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dc.contributor.authorSmonou, I.en
dc.contributor.authorKhan, S.en
dc.contributor.authorFoote, C. S.en
dc.contributor.authorElemes, Y.en
dc.contributor.authorMavridis, I. M.en
dc.contributor.authorPantidou, A.en
dc.contributor.authorOrfanopoulos, M.en
dc.date.accessioned2015-11-24T16:46:05Z-
dc.date.available2015-11-24T16:46:05Z-
dc.identifier.issn0002-7863-
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/9028-
dc.rightsDefault Licence-
dc.subjecttriazolinedione-olefin reactionsen
dc.subjectsinglet oxygenen
dc.subjectene-reactionen
dc.subjectphoto-oxidationen
dc.subjectlow-temperatureen
dc.subjectchemistryen
dc.subjectmechanismen
dc.subjectn-phenyl-1,2,4-triazoline-3,5-dioneen
dc.subjectdependenceen
dc.subjectindenesen
dc.titleReactions of Phenyltriazolinedione with Alkenes - Stereochemistry of Methanol Adducts to Aziridinium Imide Intermediatesen
heal.typejournalArticle-
heal.type.enJournal articleen
heal.type.elΆρθρο Περιοδικούel
heal.identifier.primaryDoi 10.1021/Ja00132a006-
heal.identifier.secondary<Go to ISI>://A1995RJ03500006-
heal.identifier.secondaryhttp://pubs.acs.org/doi/pdfplus/10.1021/ja00132a006-
heal.languageen-
heal.accesscampus-
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.publicationDate1995-
heal.abstractThe addition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and the stereochemistry of methanol/PTAD adduct formation with cis- and trans-2-butenes, 1-methylcyclopentene, (E)-2-methyl-2-butene-1,1,1-d(3), and substituted indenes (indene, 2-methylindene, 2,3-dimethylindene) have been investigated. There is no loss of stereochemistry in the addition of MeOH and PTAD to butenes, 1-methylcyclopentene, 2-methyl-2-butene, and indene. However, in methyl-substituted indenes 9 and 14, loss of stereochemistry at the reaction center is observed. An aziridinium imide (AI) is proposed as an intermediate in all these systems. The stability of the AI intermediate and its equilibration with an open zwitterion depend on the particular system. Only in the benzylically-stabilized tertiary indenes is the open zwitterion stable enough to cause loss of stereochemistry.en
heal.publisherAmerican Chemical Societyen
heal.journalNameJ Am Chem Socen
heal.journalTypepeer reviewed-
heal.fullTextAvailabilityTRUE-
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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