Cope rearrangement of cis-cyclonona-1,2,6-triene

Abstract

The Cope rearrangement of cis-cyclonona-1,2,6-triene to 2,3-divinylcyclopentene has been studied in the gas phase at pressures from 0·05 to 0·10 torr and in the temperature range 146 to 181°C. The reaction is quantitative, homogeneous, and kinetically first order. The rearrangement is almost certainly unimolecular. The high-pressure rate constants obtained at ten temperatures fit the Arrhenius equation k= 10^12·47 exp (–31,680 cal./RT) sec.^–1. The magnitudes of these Arrhenius parameters are discussed in relation to those reported for other Cope rearrangements.