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

ABSTRACT: 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 ¹H NMR spectra for these norbornene carboxylic anhydride molecules promotes an appreciation of constrained ring systems and factors that affect chemical shifts and coupling constants.

SUBMITTER: Birchall LT

PROVIDER: S-EPMC8675133 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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

Birchall Lee T LT Shehata Sara S Serpell Christopher J CJ Clark Ewan R ER Biagini Stefano C G SCG

Journal of chemical education 20211124 12

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 1H NMR spectra for these norbornene carboxylic anhydride molecules promotes an a ...[more]

PMID: 34924600

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