dc.contributor.author | Markoulides, Marios Savva | en |
dc.contributor.author | Ioannou, Charalambos P. | en |
dc.contributor.author | Manos, Manolis J. | en |
dc.contributor.author | Chronakis, Nikos | en |
dc.creator | Markoulides, Marios Savva | en |
dc.creator | Ioannou, Charalambos P. | en |
dc.creator | Manos, Manolis J. | en |
dc.creator | Chronakis, Nikos | en |
dc.date.accessioned | 2019-11-21T06:21:23Z | |
dc.date.available | 2019-11-21T06:21:23Z | |
dc.date.issued | 2012 | |
dc.identifier.issn | 2046-2069 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55836 | |
dc.description.abstract | Optimum 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 C60 led to the efficient and clean formation of the corresponding Diels-Alder cycloadducts. Specifically for [60]fullerene, the short-chain C60 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] C60 monoadduct at room temperature or in refluxing toluene and a low product yield (13%) was only obtained at a temperature of 45-50 °C. © 2012 The Royal Society of Chemistry. | en |
dc.source | RSC Advances | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84871061005&doi=10.1039%2fc2ra22502f&partnerID=40&md5=a68b8d317ad73f29434a7570e4958b14 | |
dc.subject | Room temperature | en |
dc.subject | Iodine | en |
dc.subject | Complexation | en |
dc.subject | Zinc | en |
dc.subject | Ultrasonic irradiation | en |
dc.subject | Cycloadditions | en |
dc.subject | Fullerenes | en |
dc.subject | Acetone | en |
dc.subject | Cycloaddition | en |
dc.subject | Diels-Alder | en |
dc.subject | [4+2] Cycloaddition reactions | en |
dc.subject | [60] fullerene | en |
dc.subject | 18-crown-6 | en |
dc.subject | Conventional heating | en |
dc.subject | Crown ethers | en |
dc.subject | Cycloadducts | en |
dc.subject | Dienophiles | en |
dc.subject | Microwave irradiation | en |
dc.subject | Olefins | en |
dc.subject | Optimum reaction conditions | en |
dc.subject | Phase transfer catalysts | en |
dc.subject | Potassium iodide | en |
dc.subject | Product yields | en |
dc.subject | Refluxing | en |
dc.subject | Short reaction time | en |
dc.subject | Toluene | en |
dc.title | Quantitative 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]fullerene | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1039/c2ra22502f | |
dc.description.volume | 2 | |
dc.description.issue | 32 | |
dc.description.startingpage | 12269 | |
dc.description.endingpage | 12277 | |
dc.author.faculty | 002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences | |
dc.author.department | Τμήμα Χημείας / Department of Chemistry | |
dc.type.uhtype | Article | en |
dc.description.notes | <p>Cited By :3</p> | en |
dc.source.abbreviation | RSC Adv. | en |
dc.contributor.orcid | Chronakis, Nikos [0000-0002-2726-5290] | |
dc.contributor.orcid | Markoulides, Marios Savva [0000-0002-0425-2104] | |
dc.gnosis.orcid | 0000-0002-2726-5290 | |
dc.gnosis.orcid | 0000-0002-0425-2104 | |