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Título

Intramolecular hydrogen abstraction promoted by amidyl radicals. Evidence for electronic factors in the nucleophilic cyclization of ambident amides to oxocarbenium ions

AutorMartín, Ángeles ; Pérez-Martín, Inés ; Suárez, Ernesto
Fecha de publicación20-abr-2005
EditorAmerican Chemical Society
CitaciónOrganic Letters 7(10): 2027-2030 (2005)
ResumenA tandem 1,5-hydrogen atom transfer/radical oxidation/nucleophilic cyclization mechanism is proposed for the intramolecular hydrogen abstraction reaction promoted for primary carboxamidyl radicals. The electron-withdrawing capacity of the C-5 substituent can switch the reaction to give exclusively bicyclic spirolactams (6-oxa-1-azaspiro[4.5]decan-2-one) when R1 = H or spirolactones (1,6-dioxaspiro[4.5]decan-2-one) when R1 = OAc. With a substituent of medium polarity (R1 = OMe), a mixture of lactones and lactams is formed.
Descripción4 pages, 1 table, 1 scheme.-- PMID: 15876046 [PubMed].-- Printed version published May 12, 2005.
Supporting information available: Detailed experimental procedures and spectral and analytical data for compounds 1-16, 19, and precursors.-- Available at: http://pubs.acs.org/doi/suppl/10.1021/ol050526u
Versión del editorhttp://dx.doi.org/10.1021/ol050526u
URIhttp://hdl.handle.net/10261/13660
DOI10.1021/ol050526u
ISSN1523-7060
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