Mechanism for Stereodifferentiation of Nucleophilic Addition to Naphthalene Radical Cations

Abstract

An optically active [4 + 2] adduct (up to 84% ee) is obtained from tetrachloro-1,2-benzoquinone and 1-alkoxy-4-phenylnaphthalene via photoinduced electron ransfer. The stereoselectivity suggests that the chiral side chain of naphthalene nucleophilically interacts with the naphthalene radical cation. The interaction was also detected by circular dichroism spectrum of the radical cation.