Internal Hydrogen Bond Formation in a syn-Hydroxyepoxide

Science  05 Feb 1982:
Vol. 215, Issue 4533, pp. 695-696
DOI: 10.1126/science.215.4533.695


The existence of an internal hydrogen bond in a compound representative of a syn diol epoxide (a possible intermediate in chemical carcinogenesis by certain polycyclic aromatic hydrocarbons) has been demonstrated by x-ray crystallographic and nuclear magnetic resonance studies. This internal hydrogen bond was found in 3,4-epoxy-2-methyl-1,2,3,4-tetrahydro-1-naphthol and was shown to persist in dioxane-water solutions containing up to 80 mole percent water. In this structure, the 1-hydroxy and 2-methyl groups are shown to occupy axial positions. In the anti diol epoxide, which has no internal hydrogen bond, analogous groups are equatorial. Crystals of the compound were unstable in the x-ray beam while the data were being collected (even at low temperatures), presumably as a result of decomposition.