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dc.contributor.authorMarkoulides, M. S.en
dc.contributor.authorIoannou, C. P.en
dc.contributor.authorManos, M. J.en
dc.contributor.authorChronakis, N.en
dc.date.accessioned2015-11-24T16:45:49Z-
dc.date.available2015-11-24T16:45:49Z-
dc.identifier.issn2046-2069-
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/8990-
dc.rightsDefault Licence-
dc.subjectdiels-alder reactionen
dc.subjectmechanochemical synthesisen
dc.subjectsulfur-dioxideen
dc.subjecto-quinodimethaneen
dc.subjectfullerene dimeren
dc.subjectsolar-cellsen
dc.subjectsingle bonden
dc.subjectc-60en
dc.subjectexpansionen
dc.subjectstereochemistryen
dc.titleQuantitative preparation of 3,4-di(methylene)tetrahydrothiophene-1,1-dioxide by Zn-induced 1,4-debromination. A valuable 6-C reactive diene in [4+2] cycloadditions with DMAD and [60]fullereneen
heal.typejournalArticle-
heal.type.enJournal articleen
heal.type.elΆρθρο Περιοδικούel
heal.identifier.primaryDoi 10.1039/C2ra22502f-
heal.identifier.secondary<Go to ISI>://000312148500038-
heal.identifier.secondaryhttp://pubs.rsc.org/en/content/articlepdf/2012/ra/c2ra22502f-
heal.languageen-
heal.accesscampus-
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.publicationDate2012-
heal.abstractOptimum reaction conditions for the quantitative preparation of the highly reactive 3,4-di(methylene) tetrahydrothiophene-1,1-dioxide are described. The method involves the zinc-induced 1,4-debromination of 3,4-bis(bromomethyl)-2,5-dihydrothiophene-1,1-dioxide in acetone solvent either by using conventional heating, microwave or ultrasonic irradiation. The [4+2] cycloaddition reaction of 3,4-di(methylene) tetrahydrothiophene-1,1-dioxide with dienophiles such as DMAD and C-60 led to the efficient and clean formation of the corresponding Diels-Alder cycloadducts. Specifically for [60]fullerene, the short-chain C-60 monoadduct was formed in a short reaction time and in high overall yield (56%). In contrast, the iodine-induced 1,4-debromination using KI in toluene, in the presence of 18-crown-6 as a phase transfer catalyst, failed to give the corresponding [4+2] C-60 monoadduct at room temperature or in refluxing toluene and a low product yield (13%) was only obtained at a temperature of 45-50 degrees C.en
heal.publisherRoyal Society of Chemistryen
heal.journalNameRsc Advancesen
heal.journalTypepeer reviewed-
heal.fullTextAvailabilityTRUE-
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά). ΧΗΜ

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