Intramolecular photoarylation of alkenes by phenyl cations

V Dichiarante, M Fagnoni, M Mella…

Index: Dichiarante, Valentina; Fagnoni, Maurizio; Mella, Mariella; Albini, Angelo Chemistry - A European Journal, 2006 , vol. 12, # 14 p. 3905 - 3915

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Citation Number: 31

Abstract

Abstract Acetone-sensitized irradiation of various o-chlorophenyl allyl ethers in polar solvents led to either (dihydro) benzofurans or chromanes. The reaction appeared to involve photoheterolysis of the aryl [BOND] Cl bond followed by phenyl cation addition onto the tethered double bond either in 5-exo or 6-endo modes. The adduct cation gave the end products by deprotonation; addition of chloride anion or of the solvent, depending on the ...