Title: Prediction of Thermal Isomerization Temperatures of Substituted Benzocyclobutenes to o-Quinodimethanes by Semi-Empirical Molecular Orbital Calculation
VOLUME: 8 ISSUE: 2
Author(s):Keisuke Chino and Takeshi Endo
Affiliation:Research Laboratory of Resources Utilization, Tokyo Institute of Technology, Nagatsuta-cho 4259, Midoriku, Yokohama 226-8502, Japan.
Keywords:Bezocyclobutene, o-quinodimethane, thermal isomerization temperature, prediction, activation energy, semiempirical molecular orbital calculation, captodative effect, aminomethane, Diels-Alder reaction, cyanobenzocyclobutene
Abstract: Bezocyclobutenes are useful compounds as precursors to o-quinodimethanes, which are highly reactive dienes. However, the thermal isomerization temperatures(IT) of substituted benzocyclobutenes to o-quinodimethanes have not been predictable based on the simple substituent effect. In this paper, we provide a simple method to predict the IT of benzocyclobutenes by calculation of the activation energies using a semi-empirical molecular orbital calculation. ITs of the various substituted benzocyclobutenes were estimated by this method.
