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  • Title: The cyclopropyl group as a hypersensitive probe in the singlet oxygen ene reaction mechanism.
    Author: Alberti MN, Orfanopoulos M.
    Journal: Org Lett; 2008 Jun 19; 10(12):2465-8. PubMed ID: 18489176.
    Abstract:
    Cyclopropyl-substituted olefins are employed as mechanistic probes in the singlet oxygen-alkene ene reaction. In MeOH and aprotic solvents [CHCl(3), (CH(3))(2)CO, CH(3)CN], only the allylic hydroperoxides bearing an intact cyclopropyl group are detected. The reaction mechanism is independent of solvent polarity. Our findings, to a certain experimental limit, exclude a biradical or dipolar intermediate.
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