The cycloaddition reactions of unsaturated esters with cyclopentadiene on γ-alumina

Richard M. Pagni, George Kabalka, George Hondrogiannis, Satinder Bains, Peter Anosike, Robert Kurt

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The Diels-Alder reaction of cyclopentadiene (CP) with methyl acrylate (MA), dimethyl maleate (DMM), and dimethyl fumarate (DMF) on alumina of varying activity has been examined. The diastereoselectivity of the reaction of CP with MA is markedly dependent on the activity of the alumina. Two factors account for these changes: (1) the nature and number of the catalytic sites on the surface, and (2) the observed reversibility of the Diels-Alder reaction on the more activated alumina. The reaction of CP with MA has been used to measure the Ω value of the surface of unactivated alumina.

Original languageEnglish (US)
Pages (from-to)6743-6756
Number of pages14
JournalTetrahedron
Volume49
Issue number31
DOIs
StatePublished - Jul 30 1993

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Cyclopentanes
Cycloaddition
Aluminum Oxide
Cycloaddition Reaction
Esters
Activated alumina
Catalytic Domain
methyl acrylate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The cycloaddition reactions of unsaturated esters with cyclopentadiene on γ-alumina. / Pagni, Richard M.; Kabalka, George; Hondrogiannis, George; Bains, Satinder; Anosike, Peter; Kurt, Robert.

In: Tetrahedron, Vol. 49, No. 31, 30.07.1993, p. 6743-6756.

Research output: Contribution to journalArticle

Pagni, RM, Kabalka, G, Hondrogiannis, G, Bains, S, Anosike, P & Kurt, R 1993, 'The cycloaddition reactions of unsaturated esters with cyclopentadiene on γ-alumina', Tetrahedron, vol. 49, no. 31, pp. 6743-6756. https://doi.org/10.1016/S0040-4020(01)80418-X
Pagni, Richard M. ; Kabalka, George ; Hondrogiannis, George ; Bains, Satinder ; Anosike, Peter ; Kurt, Robert. / The cycloaddition reactions of unsaturated esters with cyclopentadiene on γ-alumina. In: Tetrahedron. 1993 ; Vol. 49, No. 31. pp. 6743-6756.
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