Regiochemistry and stereochemistry of intramolecular [2+ 2] photocycloaddition of carbon-carbon double bonds to cyclohexenones

…, M Nagler, Y Sahali, N Haddad

Index: Becker, D.; Nagler, M.; Sahali, Y.; Haddad, N. Journal of Organic Chemistry, 1991 , vol. 56, # 14 p. 4537 - 4543

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Citation Number: 31

Abstract

The intramolecular [2+ 21 photocycloaddition mechanism of alkenes tethered by a three- methylene chain to cyclohexenones has been studied. It was found that the reversion from a 1, l-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,% carbon of the enone ...