Thermal Isomerizations of <i>cis</i>,<i>anti</i>,<i>cis</i>-Tricyclo[7.4.0.0^2,8]tridec-10-ene

Abstract

<i>cis</i>,<i>anti</i>,<i>cis</i>-Tricyclo­[7.4.0.0^2,8]­tridec-10-ene (<b>13TCT</b>) undergoes [1,3] sigmatropic rearrangements at 315 °C in the gas phase to the <i>si</i> product <b>1</b> and to the <i>sr</i> product <b>2</b> with <i>si</i>/<i>sr</i> = 2.1. The dominant thermal isomerization process, however, is epimerization at C8 to afford product <b>3</b>. That stereomutation at C8 occurs 50% faster than the <i>si</i> and <i>sr</i> shifts combined