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dc.contributor.author
Vallejos, Margarita  
dc.contributor.author
Grimblat, Nicolas  
dc.contributor.author
Pellegrinet, Silvina Carla  
dc.date.available
2017-11-24T19:27:21Z  
dc.date.issued
2014-08  
dc.identifier.citation
Vallejos, Margarita; Grimblat, Nicolas; Pellegrinet, Silvina Carla; Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study; Royal Society of Chemistry; RSC Advances; 4; 68; 8-2014; 36385-36400  
dc.identifier.issn
2046-2069  
dc.identifier.uri
http://hdl.handle.net/11336/29060  
dc.description.abstract
We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and catalyzed methodologies. Moderate to excellent exo-stereoselectivities were obtained in all cases. The theoretical study of the thermal reactions sheds some light on the intriguing substituent effects observed experimentally. A variety of substituted 5-norbornen-2-ols were easily generated by subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Royal Society of Chemistry  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc/2.5/ar/  
dc.subject
Diels-Alder  
dc.subject
Alkenylboronates  
dc.subject
Dft  
dc.subject
Reversibility  
dc.subject.classification
Otras Ciencias Químicas  
dc.subject.classification
Ciencias Químicas  
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS  
dc.title
Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2017-11-16T14:53:10Z  
dc.identifier.eissn
2046-2069  
dc.journal.volume
4  
dc.journal.number
68  
dc.journal.pagination
36385-36400  
dc.journal.pais
Reino Unido  
dc.journal.ciudad
Cambridge  
dc.description.fil
Fil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina  
dc.description.fil
Fil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina  
dc.description.fil
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina  
dc.journal.title
RSC Advances  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/C4RA07415G#!divAbstract  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/c4ra07415g  

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