
%0 Journal Article
%A Cameron, Donald W. 
%A Heisey, Ross M. 
%T Geometrically Specific Hydrogen Transfer in the Reaction of Terminally Alkyl-Substituted 1,3-Dienes with 1,4-Quinones
%J Australian Journal of Chemistry
%D 2000/05/11
%V 53
%N 2
%P 109-121
%K Dienes; quinones; cycloaddition; hydrogen transfer.
%R https://doi.org/10.1071/CH00027
%U https://www.publish.csiro.au/paper/CH00027 
%X Reaction of certain geometrically defined 1,1-dioxy-4-alkyl- and -4,4-dialkyl-substituted buta-1,3-dienes with halogenated quinones does not involve Diels&#8211;Alder or Michael addition chemistry. Instead, rapid competitive oxidation of the dienes to give 2,4-dienoate esters was observed. This new reaction involves strong spatial association between diene and quinone, hydrogen being transferred specifically from the (4E)-alkyl group. Its scope is compared with addition of the same terminally substituted dienes towards the reactive non-quinonoid dienophile tetracyanoethylene. 
