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dc.date.accessioned | 2021-11-29T14:52:18Z | |
dc.date.available | 2021-11-29T14:52:18Z | |
dc.date.issued | 2015-03 | |
dc.identifier.uri | http://sedici.unlp.edu.ar/handle/10915/128792 | |
dc.description.abstract | Abstract The clean synthesis of 6-cyano-2,2-dimethyl-2- H -1-benzopyran epoxide starting from 3-methyl-2-butenal is reported using recyclable catalysts. H₄PMo₁₁VO₄₀ (PMo₁₁V) and (PyH)₃HPMo₁₁VO₄₀ (Py₃ –PMo₁₁V) Keggin-type heteropolyacids were used to synthesize 6-cyano-2,2-dimethyl-2- H -1-benzopyran in two steps with 35% yield. This is an alternative procedure to the traditional methodology with pyridine or picoline as catalyst, where 6-cyano-2,2-dimethyl-2- H -1-benzopyran is obtained by condensation of 4-cyanophenol with 1,1-diethoxy-3-methyl-2-butene. The 6-cyano-2,2-dimethyl-2- H -1-benzopyran epoxide was obtained using Jacobsen-type catalysts, and in situ generated dimethyldioxirane (DMD) as oxidizing agent, that in comparison to m -CPBA/4-NMO and NaOCl/4-PPNO did not degrade the catalyst. In presence of 4-phenylpyridine N -oxide (4-PPNO) at 4 °C, enantioselectivities of 87% for 3S,4S-epoxide and 68% for 3R,4R-epoxide were obtained with the S,S- and R,R-Jacobsen catalysts, respectively. Overall yield was approximately 17% for 3S,4S-epoxide. | en |
dc.format.extent | 11-16 | es |
dc.language | en | es |
dc.subject | Heteropolyacids | es |
dc.subject | Jacobsen-type catalyst | es |
dc.subject | Sustainable synthesis | es |
dc.subject | 6-Cyano-2,2-dimethyl-2-H-1-benzopyran | es |
dc.subject | Chromene epoxide | es |
dc.title | Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation | en |
dc.type | Articulo | es |
sedici.identifier.other | doi:10.1016/j.molcata.2014.11.027 | es |
sedici.identifier.issn | 1381-1169 | es |
sedici.creator.person | Romanelli, Gustavo Pablo | es |
sedici.creator.person | Sathicq, Ángel Gabriel | es |
sedici.creator.person | Vázquez, Patricia Graciela | es |
sedici.creator.person | Villa, Aída Luz | es |
sedici.creator.person | Alarcón, Edwin | es |
sedici.creator.person | Grajales, Edwing | es |
sedici.creator.person | Cubillos, Jairo | es |
sedici.subject.materias | Ciencias Exactas | es |
sedici.subject.materias | Química | es |
sedici.description.fulltext | true | es |
mods.originInfo.place | Facultad de Ciencias Exactas | es |
mods.originInfo.place | Centro de Investigación y Desarrollo en Ciencias Aplicadas | es |
sedici.subtype | Articulo | es |
sedici.rights.license | Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0) | |
sedici.rights.uri | http://creativecommons.org/licenses/by-nc-sa/4.0/ | |
sedici.description.peerReview | peer-review | es |
sedici.relation.journalTitle | Journal of Molecular Catalysis A: Chemical | es |
sedici.relation.journalVolumeAndIssue | vol. 398 | es |