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Lithium aluminum hydride reduction of N-phenylanthranilic acid followed by O-acetylation gave an authentic sample of the acetate.

The photocycloaddition of acetone to íro«s-l,2-dicyanoethylene (f-DCE) and cis-1,2-dicyanoethylene (c-DCE) to yield oxetanes 1 and 2, respectively, has been studied in detail. The photocycloaddition, although inefficient, is stereospecific. Kinetic analysis reveals that the reaction occurs by attack of singlet acetone on the ground-state olefin. At low DCE concentrations, acetone triplet-sensitized cis-trans isomerization of DCE also occurs.The stereospecificity of oxetane formation can be rationalized in terms of simple MO models of the , * excited state of alkyl ketones. Possible factors causing the inefficiency of the photocycloaddition reaction are discussed.

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