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Short access to belt compounds with spatially close C=C bonds and their transannular reactions
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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.
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CAMPS GARCÍA, Pelayo, GÓMEZ NADAL, Tània, OTERMIN ESTERAS, Ane, FONT BARDIA, Ma. mercedes, ESTARELLAS, Carolina, LUQUE GARRIGA, F. xavier. Short access to belt compounds with spatially close C=C bonds and their transannular reactions. _Chemistry-A European Journal_. 2015. Vol. 21, núm. 40, pàgs. 14036-14046. [consulta: 24 de gener de 2026]. ISSN: 0947-6539. [Disponible a: https://hdl.handle.net/2445/164578]