The cyclopropyl group as a hypersensitive probe in the singlet oxygen ene reaction mechanism.
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.
Alberti
Mariza N
MN
Department of Chemistry, University of Crete, Voutes-Heraklion, Crete, Greece.
Orfanopoulos
Michael
M
D000475:Alkenes / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry*; D015394:Molecular Structure; D026082:Singlet Oxygen / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D000475:Alkenes; D003521:Cyclopropanes; D012997:Solvents; D026082:Singlet Oxygen; D006861:Hydrogen Peroxide