title: Experimental and theoretical studies of Diels-Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene.
abstract: The Diels-Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene yields a mixture of carbodiene Diels-Alder adducts. B3LYP/6-31G(d) simulations indicate that the conversion of addends into methyl (1R*,2S*,3S*,4R*)-2-nitro-3-(4-nitrophenyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylate occurs via two-stage heterodiene Diels-Alder reaction and (in a second step) skeleton rearrangement of the primary cycloadduct, whereas the reaction leading to methyl (1R*,2R*,3R*,4R*)-2-nitro-3-(4-nitrophenyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylate is a single-step process.
authors.affiliation: Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland.
authors.forename: Radomir
authors.initials: R
authors.lastname: Jasiński
authors.affiliation: Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Kwiatkowska
authors.affiliation: Department of Inorganic Chemistry, University of Chemistry and Technology, F. Engels 7, 153000 Ivanovo, Russia.
authors.forename: Valentin
authors.initials: V
authors.lastname: Sharnin
authors.affiliation: Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland.
authors.forename: Andrzej
authors.initials: A
authors.lastname: Barański
keywords: B3LYP/6–31G(d) calculations; Cyclopentadiene; Diels–Alder reaction; Nitroalkene