2816-25-3Relevant articles and documents
Mechanistic insight into the palladium-catalyzed 1,4-oxidation of 1,3-dienes to 1,4-dicarboxy-alk-2-enes
Eastgate, Martin D.,Buono, Frederic G.
experimental part, p. 5958 - 5961 (2009/12/08)
Side products get involved: The 1,4-oxidation of a diene transforms a simple hydrocarbon into an extremely useful intermediate. A complex formed in situ between palladium and a bicyclic Diels-Alder adduct, which is produced as a side product during the re
Improved Palladium-Catalyzed 1,4-Haloacyloxylation and 1,4-Diacyloxylation of Cyclic Conjugated Dienes
Baeckvall, Jan-E.,Granberg, Kenneth L.,Hopkins, R. Bruce
, p. 492 - 499 (2007/10/02)
Improved procedures for the palladium-catalyzed 1,4-oxidation of cyclic conjugated dienes have been developed.In the new procedures the reactions are performed in acetone or ethyl acetate in the presence of the appropriate carboxylic acid.Thus, palladium-catalyzed oxidations of cyclic conjugated dienes in acetone in the presence of a carboxylic acid and lithium chloride using p-benzoquinone as the oxidant leads to an efficient cis-1,4-chloroacyloxylation.If the reaction is performed in the absence of lithium chloride, but under otherwise identical conditions, a 1,4-diacyloxylation of the conjugated diene takes place. 1,4-Bromoacyloxylation occurs if lithium bromide is used in place of lithium chloride in the palladium-catalyzed oxidation.These new procedures allow the use of a variety of carboxylates in Pd-catalyzed haloacyloxylations and diacyloxylations.
