Carbonyl Oxide Chemistry. The NIH Shift

Article abstract of DOI:10.1021/ja00316a037

Benzophenone oxide has been shown to oxidize 1-chloronaphthalene and p-xylene with accompanying NIH shift of chlorine and methyl, respectively.Similar oxidation of toluene leads to a mixture of o-,p-, and m-cresols while N-acetyl-L-phenylalanine ethyl ester is oxidized to the corresponding tyrosine derivative.The results are discussed in terms of their relationship to the "activation" of polycyclic aromatic hydrocarbons in polluted atmospheres and the possible production of mutagens/carcinogens.