Please use this identifier to cite or link to this item:
logo share SHARE BASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE

Intramolecular hydrogen abstraction. (Diacetoxyiodo)benzene, a useful reagent for the remote functionalization of non-activated carbon atoms

AuthorsDorta, Rosa L.; Francisco, Cosme G. CSIC; Hernández, Rosendo CSIC; Salazar, José A.; Suárez, Ernesto CSIC ORCID
Issue Date1990
PublisherTurpin Distribution
CitationJournal of Chemical Research(S) 1990: 240-241 (1990)
AbstractIn previous papers we have reported that the system (diacetoxyiodo)benzene and iodine is more efficient and convenient to generate alkoxyl radicals from alcohols than those constituted from heavy metal derivatives (e.g. Pb(IV), Hg (II) and Ag(I)) and iodine usually employed in such reactions. We now report that in situ photolyses with visible light of several hydroxy compounds such as (-)-6,6-dimethylbicyclo[3.1.1]heptan-2β-ol [(-)-cis-nopinol] (1), 2-ethoxycarbonylmethyl-6,6-dimethylbicyclo[3.1.1]heptan-2β-ol (2), cedrol (5), isolongifolol /8), the hydrindane derivative (12), labdane-8α,15-diol (18), methyl 8α-hydroxylabdan-15-oate (19), labdanolic acid (20), methyl 3β-hydroxy-friedelan-29-oate (27) and friedelane-3b,30-diol 30-acetate (30) in the presence of (diacetoxyiodo)benzene and iodine lead to alkoxyl radicals which undergo intramolecular abstraction of suitably positioned hidrogen atoms to produce γ-functionalized derivatives.
Description2 pages, 1 scheme.-- Paper in Journal of Chemical Research(M) available at:
Appears in Collections:(IPNA) Artículos

Files in This Item:
File Description SizeFormat
JCR-1990-0-240.pdf186,98 kBAdobe PDFThumbnail
Show full item record
Review this work

Page view(s)

checked on Jul 5, 2022


checked on Jul 5, 2022

Google ScholarTM


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.