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Intramolecular 1,5- versus 1,6-hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrate models

AuthorsFrancisco, Cosme G. ; Freire, Raimundo ; Herrera, Antonio J. ; Pérez-Martín, Inés ; Suárez, Ernesto
Issue Date4-May-2002
PublisherAmerican Chemical Society
CitationOrganic Letters 4(11): 1959-1961 (2002)
AbstractThe alkoxy radical generated by reaction of 3,7-anhydro-2-deoxyoctitols with (diacetoxyiodo)benzene (DIB) and iodine abstracts regioselectively either the proton at C7 or that at C4 depending on the electronegativity of the substituent at C4. The correct election of this substituent can switch the reaction to give 2,9-dioxabicyclo[3.3.1]nonane or hexahydro-2H-furo[3,2-b]pyran ring systems.
Description3 pages, 1 table, 2 schemes.-- PMID: 12027657 [PubMed].-- Printed version published May 30, 2002.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol025981u
Erratum to this paper published in: Org. Lett. 4(19): 3337 (2002), http://dx.doi.org/10.1021/ol020134c
Publisher version (URL)http://dx.doi.org/10.1021/ol025981u
Appears in Collections:(IPNA) Artículos
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