Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study

[Image: see text] The thermal equilibration of himic anhydride [IUPAC (2-endo,3-endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride] to (2-exo,3-exo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and subsequent recrystallization of the exo-product can be performed as a standard...

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Autores principales: Birchall, Lee T., Shehata, Sara, Serpell, Christopher J., Clark, Ewan R., Biagini, Stefano C. G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and Division of Chemical Education, Inc. 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8675133/
https://www.ncbi.nlm.nih.gov/pubmed/34924600
http://dx.doi.org/10.1021/acs.jchemed.1c00661
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author Birchall, Lee T.
Shehata, Sara
Serpell, Christopher J.
Clark, Ewan R.
Biagini, Stefano C. G.
author_facet Birchall, Lee T.
Shehata, Sara
Serpell, Christopher J.
Clark, Ewan R.
Biagini, Stefano C. G.
author_sort Birchall, Lee T.
collection PubMed
description [Image: see text] The thermal equilibration of himic anhydride [IUPAC (2-endo,3-endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride] to (2-exo,3-exo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and subsequent recrystallization of the exo-product can be performed as a standard undergraduate laboratory experiment requiring minimal equipment. The interpretation of the (1)H NMR spectra for these norbornene carboxylic anhydride molecules promotes an appreciation of constrained ring systems and factors that affect chemical shifts and coupling constants.
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spelling pubmed-86751332021-12-17 Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study Birchall, Lee T. Shehata, Sara Serpell, Christopher J. Clark, Ewan R. Biagini, Stefano C. G. J Chem Educ [Image: see text] The thermal equilibration of himic anhydride [IUPAC (2-endo,3-endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride] to (2-exo,3-exo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and subsequent recrystallization of the exo-product can be performed as a standard undergraduate laboratory experiment requiring minimal equipment. The interpretation of the (1)H NMR spectra for these norbornene carboxylic anhydride molecules promotes an appreciation of constrained ring systems and factors that affect chemical shifts and coupling constants. American Chemical Society and Division of Chemical Education, Inc. 2021-11-24 2021-12-14 /pmc/articles/PMC8675133/ /pubmed/34924600 http://dx.doi.org/10.1021/acs.jchemed.1c00661 Text en © 2021 The Authors. Published by American Chemical Society and Division of Chemical Education, Inc. https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Birchall, Lee T.
Shehata, Sara
Serpell, Christopher J.
Clark, Ewan R.
Biagini, Stefano C. G.
Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
title Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
title_full Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
title_fullStr Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
title_full_unstemmed Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
title_short Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
title_sort himic anhydride: a retro diels–alder reaction for the organic laboratory and an accompanying nmr study
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8675133/
https://www.ncbi.nlm.nih.gov/pubmed/34924600
http://dx.doi.org/10.1021/acs.jchemed.1c00661
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