1,3-Shift with inversion in a norbornadiene to cycloheptatriene rearrangement
Abstract
syn-Methoxynorbornadiene (5) rearranges thermally via formal 1,3-Sigmatropic shift to a set of cycloheptatrienes different to those obtained from anti-methoxynorbornadiene (6); the ca. 95% selective migration of C-7 to the double bond anti to the methoxy group in both isomers suggests a preference for a 1,3-shift with inversion at C-7.