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....

Descripción completa

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
_version_ 1782380192370524160
author Jasiński, Radomir
Kwiatkowska, Magdalena
Sharnin, Valentin
Barański, Andrzej
author_facet Jasiński, Radomir
Kwiatkowska, Magdalena
Sharnin, Valentin
Barański, Andrzej
author_sort Jasiński, Radomir
collection PubMed
description 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]
format Online
Article
Text
id pubmed-4495048
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher Springer Vienna
record_format MEDLINE/PubMed
spelling pubmed-44950482015-07-09 Experimental and theoretical studies of Diels–Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene Jasiński, Radomir Kwiatkowska, Magdalena Sharnin, Valentin Barański, Andrzej Monatsh Chem Original Paper 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] Springer Vienna 2013-01-09 2013 /pmc/articles/PMC4495048/ /pubmed/26166878 http://dx.doi.org/10.1007/s00706-012-0885-3 Text en © The Author(s) 2012 https://creativecommons.org/licenses/by/2.0/ Open AccessThis article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution, and reproduction in any medium, provided the original author(s) and the source are credited.
spellingShingle Original Paper
Jasiński, Radomir
Kwiatkowska, Magdalena
Sharnin, Valentin
Barański, Andrzej
Experimental and theoretical studies of Diels–Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene
title Experimental and theoretical studies of Diels–Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene
title_full Experimental and theoretical studies of Diels–Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene
title_fullStr Experimental and theoretical studies of Diels–Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene
title_full_unstemmed Experimental and theoretical studies of Diels–Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene
title_short Experimental and theoretical studies of Diels–Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene
title_sort experimental and theoretical studies of diels–alder reaction between methyl (z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene
topic Original Paper
url 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
work_keys_str_mv AT jasinskiradomir experimentalandtheoreticalstudiesofdielsalderreactionbetweenmethylz2nitro34nitrophenyl2propenoateandcyclopentadiene
AT kwiatkowskamagdalena experimentalandtheoreticalstudiesofdielsalderreactionbetweenmethylz2nitro34nitrophenyl2propenoateandcyclopentadiene
AT sharninvalentin experimentalandtheoreticalstudiesofdielsalderreactionbetweenmethylz2nitro34nitrophenyl2propenoateandcyclopentadiene
AT baranskiandrzej experimentalandtheoreticalstudiesofdielsalderreactionbetweenmethylz2nitro34nitrophenyl2propenoateandcyclopentadiene

Ejemplares similares