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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: https://doi.org/10.1002/ejoc.201601618 |
It is part of: | European Journal of Organic Chemistry, 2017, vol. 2017, num. 12, p. 1594-1603 |
URI: | http://hdl.handle.net/2445/163240 |
Related resource: | https://doi.org/10.1002/ejoc.201601618 |
ISSN: | 1434-193X |
Appears in Collections: | Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) |
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