Molecular rearrangements of excited states generated by intramolecular dioxetane scission. Photochemistry without light. Mechanistic and exploratory organic …

HE Zimmerman, GE Keck…

Index: Zimmerman,H.E. et al. Journal of the American Chemical Society, 1976 , vol. 98, # 18 p. 5574 - 5581

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Citation Number: 30

Abstract

Abstract: A series of 1-methylene-4, 4-diphenyl-2, 5-cyclohexadienes was synthesized. Singlet oxygen reacted selectively, with the exocyclic double bond affording a parallel series of dioxetanes. Thermolysis of the dioxetanes gave, in each case, 4, 4-diphe-nyl-2, 5- cyclohexadienone, 6, 6-diphenylbicyclo [3.1. O] hex-3-en-2-one, and the ketone derived from exocyclic double bond fission (ie, acetone, acetophenone, m-methoxyacetophenone, ...