Studies dealing with the excited-state behavior of substituted 8-oxabicyclo [3.2. 1] oct-6-en-2-ones

A Padwa, L Zhi, GE Fryxell

Index: Padwa, Albert; Zhi, Lin; Fryxell, Glen E. Journal of Organic Chemistry, 1991 , vol. 56, # 3 p. 1077 - 1083

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Citation Number: 9

Abstract

A series of 8-oxabicyclo [3.2. 1] od-6-en-2-ones was prepared by the rhodium (I1)-catalyzed cyclization-cycloaddition reaction of a-diazopentanedione with various alkynes. The photochemical behavior of these oxabicyclic enones was investigated. Both direct and sensitized photolysis cleanly results in a 1, 3-acyl shift. A slower, secondary photoprocess involving intramolecular hydrogen atom transfer and intramolecular cycloaddition of the ...