Tetrahedron p. 3329 - 3338 (1981)
Update date:2022-09-26
Topics:
Schuster, David I.
Liu, Kou-Chang
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 bicyclo<3.1.0>hex-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.
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