ウッドワード・ホフマン則
In a thermal [1,3] hydride shift, a hydride moves three atoms. The Woodward–Hoffmann rules dictate that it would proceed in an antarafacial shift. Although such a shift is symmetry allowed, the Mobius topology required in the transition state prohibits such a shift because it is geometrically impossible, which accounts for the fact that enols do not isomerize without an acid or base catalyst.