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Regiochemistry and Stereochemistry of Intramolecular Photocycloaddition of Carbon-Carbon Double Bonds to Cyclohexenones
Becker, D.,Nagler, M.,Sahali, Y.,Haddad, N.
, p. 4537 - 4543 (2007/10/02)
The intramolecular photocycloaddition mechanism of alkenes tethered by a three-methylene chain to cyclohexenones has been studied.It was found that the reversion from a 1,4-diradical intermediate to starting material is slow relative to the rate of photoadduct formation.Only "straight" closure was observed in the systems studied.For compounds 1-3 and 5, the assumption that the first bond is formed between the β-carbon of the enone and C-4' leading to a 1,4-diradical is supported.For the formation of compounds 6-11, possible mechanisms are discussed.
