The first observation of thermal transformation of strained paracyclophane into the Dewar isomer

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Masahiro Okuyama, Masakazu Ohkita and Takashi Tsuji


Abstract

The kinetic stabilization of the [4]paracyclophane structure in the 2,5-bis(dicyanomethylene)-2-ene derivative permits the first observation of thermal isomerization of a strained paracyclophane to the Dewar valence tautomer; the activation free energy for the process is 18.3 ± 0.3 kcal mol-1 at -20 °C.


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