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Title: Short access to belt compounds with spatially close C=C bonds and their transannular reactions
Author: Camps García, Pelayo
Gómez Nadal, Tània
Otermin Esteras, Ane
Font Bardia, Ma. Mercedes
Estarellas, Carolina
Luque Garriga, F. Xavier
Keywords: Reaccions químiques
Difusió de raigs X
Chemical reactions
X-ray scattering
Issue Date: 20-Aug-2015
Publisher: Wiley-VCH
Abstract: Two domino Diels-Alder adducts were obtained from 3,7-bis(cyclopenta-2,4-dien-1-ylidene)-cis-bicyclo[3.3.0]octane and dimethyl acetylenedicarboxylate or N-methylmaleimide under microwave irradiation. From the first adduct, a C20H24 diene with C2v symmetry was obtained by Zn/AcOH reduction, hydrolysis, oxidative decarboxylation and selective hydrogenation. Photochemical [2+2] cycloaddition of this diene gave a thermally unstable cyclobutane derivative, which reverts to the diene. However, both diene and cyclobutane derivatives could be identified by X-ray diffraction analysis upon irradiation of the diene crystal. New six-membered rings are formed upon transannular addition of bromine or iodine to the diene. The N-type selectivity of the addition was examined by theoretical calculations which revealed the distinct susceptibility of the doubly bonded carbon atoms to the bromine attack.
Note: Versió postprint del document publicat a:
It is part of: Chemistry-A European Journal, 2015, vol. 21, num. 40, p. 14036-14046
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ISSN: 0947-6539
Appears in Collections:Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)
Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)
Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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