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dc.contributor.authorFrancisco, Cosme G.en_US
dc.contributor.authorFreire, Raimundoen_US
dc.contributor.authorHerrera, Antonio J.en_US
dc.contributor.authorPérez-Martín, Inésen_US
dc.contributor.authorSuárez, Ernesto-
dc.date.accessioned2009-05-12T06:20:44Z-
dc.date.available2009-05-12T06:20:44Z-
dc.date.issued2007-06-12en_US
dc.identifier.citationTetrahedron 63(36): 8910-8920 (2007)en_US
dc.identifier.issn0040-4020-
dc.identifier.urihttp://hdl.handle.net/10261/12990-
dc.description11 pages, 1 table, 6 schemes.-- Printed version published Sep 3, 2007.-
dc.description.abstractThe primary alkoxyl radical generated by reaction of 1-(2-hydroxyethyl)-glycosides with (diacetoxyiodo)benzene (DIB) and iodine can undergo regioselective intramolecular hydrogen abstraction (IHA) reactions to furnish four different dioxabicyclic systems derived from carbohydrates. The results strongly suggest that the regiocontrol and feasibility of the cyclisation are dependant not only on geometric and stereoelectronic factors, but also on polar and thermochemical factors. The correct selection of the substituents at the precursors can favour the 1,6-IHA against the 1,5-IHA pathway.-
dc.description.sponsorshipThis work was supported by the investigation programmes CTQ2004-06381/BQU and CTQ20004-02367/BQU of the Dirección General de Investigación Científica y Técnica, Spain. A.J.H. and I.P.-M. thank the Ministerio de Educación y Ciencia, Spain, and the programme I3P-CSIC, respectively, for fellowships.-
dc.format.extent2373 bytes-
dc.format.extent625093 bytes-
dc.format.mimetypetext/plain-
dc.format.mimetypeapplication/pdf-
dc.language.isoengen_US
dc.publisherElsevier-
dc.rightsclosedAccessen_US
dc.titleIntramolecular 1,5- versus 1,6-hydrogen abstraction reaction promoted by alkoxyl radicals in pyranose and furanose modelsen_US
dc.typeartículoen_US
dc.identifier.doi10.1016/j.tet.2007.06.023-
dc.relation.publisherversionhttp://dx.doi.org/10.1016/j.tet.2007.06.023-
dc.contributor.funderDirección General de Investigación Científica y Técnica, DGICT (España)-
dc.contributor.funderMinisterio de Educación y Ciencia (España)-
dc.contributor.funderConsejo Superior de Investigaciones Científicas (España)-
dc.identifier.funderhttp://dx.doi.org/10.13039/501100003339es_ES
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