A syn hydroxy-epoxide derived from the naphthalene system (1-beta-hydroxy-2-alpha-methyl-3,4-bet-epoxy-1,2,3,4-tetrahydronaphthalene), structurally related to the cis diol epoxide metabolite of certain polycyclic aromatic hydrocarbons such as benzo(a)pyrene, has been synthesized. From X-ray crystallographic data, it has been shown that an intramolecular hydrogen bond between the benzyl hydroxyl and the epoxide oxygen exists in the crystalline state. Studies will be carried out to determine the extent to which this intramolecular hydrogen bonding exists in aqueous solutions, and whether or not such hydrogen bonding is important in the solution chemistry of this model compound. An ongoing study of the reactions of diol epoxides derived from polycyclic aromatic hydrocarbons will be continued.