Kinetic and Thermodynamic Studies of the Thermal Electrocyclic Interconversions of Perfluorinated Dienes and Cyclobutenes

Article abstract of DOI:10.1021/ja00235a032

Detailed kinetic and thermodynamic analyses were carried out for the thermal interconversions of (Z,Z)- and (E,E)-perfluoro-2,4-hexadienes with trans-perfluoro-3,4-dimethylcyclobutene, (E,Z)-perfluoro-2,4-hexadiene with perfluoro-cis-3,4-dimethylcyclobutene, (Z,Z)- and (E,E)-perfluoro-3,5-octadienes with trans-perfluoro-3,4-diethylcyclobutene, and (Z)- and (E)-perfluoro-1,3-pentadiene with perfluoro-3-methylcyclobutene.In each case the (Z,Z)- or (Z)-dienes exhibited substantial kinetic advantage over the (E,E)-or (E)-dienes in their cyclization precesses.