147. Photodissociation of Halonaphthalenes in Solution: Comparative Photochemistry of 1-Iodo-, 1-Bromo-, and 1-Chloronaphthalenes

Article abstract of DOI:10.1002/hlca.19900730609

Fluorescence measurements have been used to follow the build-up of photoproducts during the direct and benzophenone-sensitized irradiation of the title compounds 1-IN, 1-BrN, and 1-ClN (HN = naphthalene).Compounds 1-IN and 1-BrN react by homolytic dissociation through their lowest triplet and singlet excited states, respectively.Compound 1-ClN does not undergo C-Cl bond fission, except through electron transfer in the presence of an amine A, ¹(1-ClN)^* + A -> (1-ClN)^-. + A⁺, then (1-ClN)^-. -> N^. + Cl^-. In the absence of this electron tranfer, 1-ClN reacts only through substitution and oxidation processes.