Illumination (λ > 325 mµ) of the ene-1,4-diones (Ia)—(Ie) in the presence of olefins and acetylenes gives derivatives of tetracyclo [8,2,1,02,9, 04,7] tridecane [e.g., (II)]. The reaction appears to involve an electrophilic 3(ππ*) state of the enedione which adds to the olefin via a transition state resembling the most stable biradical intermediate.
J. A. Barltrop and D. Giles, J. Chem. Soc. C, 1969, 105 DOI: 10.1039/J39690000105
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