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Title: Straightforward synthesis of a vicinal double bridgehead iodo trimethylsilyl octacycle: unprecedented lack of reactivity of the silyl group in front of fluoride anions.
Author: Camps García, Pelayo
Lozano Mena, David
Guitián, E.
Peña, D.
Pérez, D.
Font Bardia, Ma. Mercedes
Llamas-Saíz, A.L.
Keywords: Reaccions químiques
Cicles biogeoquímics
Chemical reactions
Biogeochemical cycles
Issue Date: 27-Mar-2017
Publisher: Wiley-VCH
Abstract: Abstract: A convenient synthesis of an octacyclic compound containing an iodo and a trimethylsilyl group in vicinal double bridgehead positions, as a possible precursor of a pyramidalized alkene, is described. The key step of the synthesis consists of a double nucleophilic substitution of two neopentyl-type iodides by cyclopentadienide anions followed by two intramolecular Diels-Alder cycloadditions. All attempts to generate the expected pyramidalized alkene from the above precursor on reac-tion with different sources of fluoride failed. This octacyclic compound, which contains two disubstituted C=C bonds, underwent a chemo- and stereoselective Pd0-catalyzed co-cyclotrimerization with dimethyl acetylenedicarb-oxylate to give a nonacyclic cyclohexadiene derivative that can be aromatized upon reaction with CsF or transformed into a related fluoride upon reaction with AgF.
Note: Versió postprint del document publicat a:
It is part of: European Journal of Organic Chemistry, 2017, vol. 2017, num. 12, p. 1594-1603
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ISSN: 1434-193X
Appears in Collections:Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)

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