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On the origin of geminal regioselectivity in the ene reaction of singlet oxygen with substituted alkenes |
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| Authors: | Waldemar Adam and Markus J Richter |
| Institution: | Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany |
| Abstract: | The geminal regioselectivity observed in the ene reaction between singlet oxygen and alkenes with anion-stabilizing groups is rationalized on the basis of a perepoxide intermediate, in which in analogy to the nucleophilic attack on protonated epoxides, the perepoxide is opened preferentially at the C---O bond weakened by the substituent. |
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