First evidence of the formation of 5,8-endoperoxide from the oxidation of 1,4-disubstituted naphthalene by singlet oxygen

Abstract

Bulky water-soluble 1,4-disubstituted naphthalenes react with singlet oxygen giving the usual 1,4- and the unexpected 5,8-endoperoxides and showing that the regioselectivity of the [4 + 2] cycloaddition of singlet oxygen depends on the steric hindrance of the substrate.