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On the Diels-Alder reactions of pentadienyl maleates and citraconates

Cayzer, Tory; Lilly, Michael; Williamson, Rachel; Paddon-Row, Michael; Sherburn, Michael

Description

Reactions between conjugated dienols and maleic anhydride provide either cis-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 via intermolecular Diels-Alder reaction followed by intramolecular esterification. Pre-forming the maleate half ester derivative followed by heating affords predominantly trans-fused lactone acids...[Show more]

CollectionsANU Research Publications
Date published: 2005
Type: Journal article
URI: http://hdl.handle.net/1885/77464
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b501446h

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