dc.contributor.author | Riala, Maria | en |
dc.contributor.author | Chronakis, Nikos | en |
dc.creator | Riala, Maria | en |
dc.creator | Chronakis, Nikos | en |
dc.date.accessioned | 2019-11-21T06:22:31Z | |
dc.date.available | 2019-11-21T06:22:31Z | |
dc.date.issued | 2013 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/56066 | |
dc.description.abstract | In this Article, we describe the synthesis of two optically pure diols bearing a 1,2-diol moiety masked as an isopropylidene acetal group and long alkyl chains comprised of 12 and 14 carbon atoms, respectively. The synthetic methodology that was developed offers a general way for the synthesis of optically pure diols with long alkyl chains. Diols (-)-4 and (-)-9 were subjected to a condensation reaction with malonyl dichloride to afford two cyclo-[2]-malonate tethers that were separated by column chromatography in optically pure form. The bismalonates (-)-4b and (-)-9b proved to be excellent tethers for the regioselective Bingel functionalization of C60, furnishing in a regioselective manner the corresponding f,sC and f,sA trans-3 bisadducts with low diastereoselectivity but in very good to excellent total yields. In both cases, the formed trans-3 bisadducts were isolated in pure form by simple column chromatography and were fully characterized. The successful acetal deprotection of the synthesized trans-3 bisadducts afforded quantitatively the corresponding polyalcohols, which represent novel chiral fullerene compounds equipped with glycol moieties. © 2013 American Chemical Society. | en |
dc.source | Journal of Organic Chemistry | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84881253361&doi=10.1021%2fjo4013173&partnerID=40&md5=e8b2c131cba9dc743138edc2fc2159b9 | |
dc.subject | methodology | en |
dc.subject | article | en |
dc.subject | chemistry | en |
dc.subject | Chromatography | en |
dc.subject | synthesis | en |
dc.subject | chemical structure | en |
dc.subject | polymerization | en |
dc.subject | carbon | en |
dc.subject | Molecular Structure | en |
dc.subject | alcohol derivative | en |
dc.subject | addition reaction | en |
dc.subject | fullerene derivative | en |
dc.subject | stereochemistry | en |
dc.subject | Regioselectivity | en |
dc.subject | stereoisomerism | en |
dc.subject | chirality | en |
dc.subject | column chromatography | en |
dc.subject | enantiomer | en |
dc.subject | malonic acid derivative | en |
dc.subject | Fullerenes | en |
dc.subject | Alcohols | en |
dc.subject | malonic acid | en |
dc.subject | Condensation reactions | en |
dc.subject | Synthetic methodology | en |
dc.subject | atom | en |
dc.subject | carbon 14 | en |
dc.subject | Carbon atoms | en |
dc.subject | Deprotection | en |
dc.subject | Diastereo-selectivity | en |
dc.subject | fullerene C60 | en |
dc.subject | Functionalizations | en |
dc.subject | Isopropylidene acetal | en |
dc.subject | Long alkyl chains | en |
dc.subject | Malonates | en |
dc.subject | phosphonium derivative | en |
dc.subject | reaction optimization | en |
dc.subject | Regio-selective | en |
dc.subject | Tetherlines | en |
dc.title | Remote functionalization of C60 with enantiomerically pure cyclo-[2]-malonate tethers bearing C12 and C14 spacers: Synthetic access to bisadducts of C60 with the inherently chiral trans-3 addition pattern | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1021/jo4013173 | |
dc.description.volume | 78 | |
dc.description.issue | 15 | |
dc.description.startingpage | 7701 | |
dc.description.endingpage | 7713 | |
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 :9</p> | en |
dc.source.abbreviation | J.Org.Chem. | en |
dc.contributor.orcid | Chronakis, Nikos [0000-0002-2726-5290] | |
dc.gnosis.orcid | 0000-0002-2726-5290 | |