A new stereospecific trans-elimination of 2-alkoxy- and 2-cycloalkoxy-tropones to alkenes and cycloalkenes: the first verification of the [s8π+a2σ+s2σ] process
Abstract
Solutions of 2-alkoxy- and 2-cycloalkoxy-tropones were heated to give alkenes and cycloalkenes respectively, without skeletal rearrangement, in good yields; deuterium labelling studies confirmed a stereospecific trans-elimination, in a [s8π+a2σ+s2σ] mode, with an interesting isotope effect and a large rate retardation.