On the Diels–Alder reactions of pentadienyl maleates and citraconates

…, MJ Lilly, RM Williamson, MN Paddon-Row…

Index: Cayzer, Tory N.; Lilly, Michael J.; Williamson, Rachel M.; Paddon-Row, Michael N.; Sherburn, Michael S. Organic and Biomolecular Chemistry, 2005 , vol. 3, # 7 p. 1302 - 1307

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Citation Number: 13

Abstract

Reactions between conjugated dienols and maleic anhydride provide eithercis-fused or trans-fused bicyclic products as major products, depending upon how the reaction is carried out. Simply mixing the two reactants together generally leads to cis-fused lactone acids in thermal reactions which proceed viaintermolecular Diels–Alder reaction followed by intramolecular esterification. Pre-forming the maleate half ester derivative followed by ...