Contrasting photochemistry of cyclopentenone and cyclohexenone
Abstract
Room-temperature irradiation of 4,4-diphenyl- and 4-methyl-4-phenyl-cyclopentenone led very efficiently to keten rearrangement products [e.g.(4)] rather than bicyclic ketones [e.g.(6)] characteristic of cyclohexenone photochemistry; at low temperatures the bicyclic ketone primary product underwent further photochemical reaction to give the keten, but the bicyclic ketone was not an intermediate at room temperature.
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