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....

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Detalles Bibliográficos
Autores principales: Jasiński, Radomir, Kwiatkowska, Magdalena, Sharnin, Valentin, Barański, Andrzej
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2013
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4495048/
https://www.ncbi.nlm.nih.gov/pubmed/26166878
http://dx.doi.org/10.1007/s00706-012-0885-3
Descripción
Sumario: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. GRAPHICAL ABSTRACT: [Image: see text]

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