56795-76-7Relevant academic research and scientific papers
EXPERIMENTAL PROOF FOR THE INTERMEDIACY OF ZWITTERIONS IN THE PATHWAY LEADING TO LUMIKETONES UPON IRRADIATION OF 2,5-CYCLOHEXADIENONES
Schuster, David I.,Liu, Kou-Chang
, p. 3329 - 3338 (2007/10/02)
Details are presented of kinetic studies, which demonstrate that a zwitterionic species is an obligatory intermediate in the photochemical rearrangement of a model 2,5-cyclohexadienone to its isomeric bicyclohex-3-en-2-one (lumiketone).In these studies, the zwitterionic intermediate has been succesfully intercepted by lithium chloride present in the mixture.In addition, studies of the temperature dependence of zwitterion-derived processes suggest that cycloreversion of the zwitterion to the starting dienone by a symmetryforbidden process in the main source of energy wastage in this system, and that this reversion becomes increasingly efficient as the temperature is raised.
