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Issue 0, 1981
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The structure of glutaconic anhydride and the synthetic utility of its Diels–Alder adduct with cyclopentadiene

Abstract

In non-polar solvents glutaconic anhydride exists predominantly as its dioxo-tautomer (1). Diels–Alder reaction with cyclopentadiene affords 3-endo-carboxynorborn-5-en-2-endo-ylacetic acid anhydride (5) having considerable synthetic potential, and which on hydrolysis gives the corresponding bis-endo-dicarboxylic acid (6a). The dimethyl ester of (6a) may be epimerised and hydrolysed to the trans-dicarboxylic acid, 3-exo-carboxynorborn-5-en-2-endo-ylacetic acid (9a). The acids (6a) and (9a) have been characterised as a γ-iodolactone (7a) and a δ-iodolactone (13), respectively.

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Article type: Paper
DOI: 10.1039/P19810000146
Citation: J. Chem. Soc., Perkin Trans. 1, 1981, 146-149
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    The structure of glutaconic anhydride and the synthetic utility of its Diels–Alder adduct with cyclopentadiene

    S. P. Briggs, D. I. Davies, R. F. Newton and D. P. Reynolds, J. Chem. Soc., Perkin Trans. 1, 1981, 146
    DOI: 10.1039/P19810000146

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