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
| dc.contributor.author | Markoulides, M. S. | en |
| dc.contributor.author | Ioannou, C. P. | en |
| dc.contributor.author | Manos, M. J. | en |
| dc.contributor.author | Chronakis, N. | en |
| dc.date.accessioned | 2015-11-24T16:45:49Z | |
| dc.date.available | 2015-11-24T16:45:49Z | |
| dc.identifier.issn | 2046-2069 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/8990 | |
| dc.rights | Default Licence | - |
| dc.subject | diels-alder reaction | en |
| dc.subject | mechanochemical synthesis | en |
| dc.subject | sulfur-dioxide | en |
| dc.subject | o-quinodimethane | en |
| dc.subject | fullerene dimer | en |
| dc.subject | solar-cells | en |
| dc.subject | single bond | en |
| dc.subject | c-60 | en |
| dc.subject | expansion | en |
| dc.subject | stereochemistry | 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 |
| heal.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 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.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | Doi 10.1039/C2ra22502f | - |
| heal.identifier.secondary | <Go to ISI>://000312148500038 | - |
| heal.identifier.secondary | http://pubs.rsc.org/en/content/articlepdf/2012/ra/c2ra22502f | - |
| heal.journalName | Rsc Advances | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2012 | - |
| heal.publisher | Royal Society of Chemistry | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |