Australian Journal of Chemistry

Geometrically specific hydrogen transfer in the reaction of terminally alkyl-substituted 1, 3-dienes with 1, 4-quinones

DW Cameron, RM Heisey

Index: Cameron, Donald W.; Heisey, Ross M. Australian Journal of Chemistry, 2000 , vol. 53, # 2 p. 109 - 121

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Citation Number: 12

Abstract

Abstract 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–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 ...