Jump to main content
Jump to site search

Issue 9, 1977
Previous Article Next Article

Conservation of the chair-like transition state by base-catalysed epimerization of meso-tetramethyl hexa-1,5-diene-2,3,4,5-tetracarboxylate prior to its Cope rearrangement

Abstract

meso-Tetramethyl hexa-1,5-diene-2,3,4,5-tetracarboxylate (5) rearranges at 20–50 °C in the presence of sodium carbonate to (E,E)-tetramethyl hexa-1,5-diene-1,2,5,6-tetracarboxylate (7), by base-catalysed epimerization followed by Cope rearrangement of the resulting (±)-tetraester (6)via the expected four-centred, chair-like transition state. In the absence of base the meso-tetraester (5) undergoes [3,3] sigmatropic rearrangement to produce (E,Z)-tetramethyl hexa-1,5-diene-1,2,5,6-tetracarboxylate (8) exclusively.

Back to tab navigation

Article information


J. Chem. Soc., Perkin Trans. 1, 1977, 1073-1075
Article type
Paper

Conservation of the chair-like transition state by base-catalysed epimerization of meso-tetramethyl hexa-1,5-diene-2,3,4,5-tetracarboxylate prior to its Cope rearrangement

C. J. Meyer and D. F. Schneider, J. Chem. Soc., Perkin Trans. 1, 1977, 1073
DOI: 10.1039/P19770001073

Search articles by author

Spotlight

Advertisements