¹³C magnetic resonance studies 70. The behavior of bicyclo[2.2.2]octenone under strongly basic conditions. A competition between retro Diels–Alder and Haller-Bauer-cleavages

15 December 1977

journal article
Published by Canadian Science Publishing in Canadian Journal of Chemistry

Vol. 55 (24) , 4184-4190
https://doi.org/10.1139/v77-593

Abstract

As a test for possible competitive α- and β-enolization in bicyclic ketones the behavior of bicyclo[2.2.2]octenone in t-BuO⁻–t-BuOH at 185 °C has been examined. The major reaction (∼90%) involves Claisen condensation followed by retro Diels-Alder elimination of ethylene and Haller–Bauer cleavage. All acidic and phenolic components, accounting for 90% of the product, have been identified and characterized, primarily by their ¹³Cmr spectra.

Keywords

MAGNETIC RESONANCE

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13C magnetic resonance studies 70. The behavior of bicyclo[2.2.2]octenone under strongly basic conditions. A competition between retro Diels–Alder and Haller-Bauer-cleavages

Abstract

Keywords

¹³C magnetic resonance studies 70. The behavior of bicyclo[2.2.2]octenone under strongly basic conditions. A competition between retro Diels–Alder and Haller-Bauer-cleavages