Transformations of perfluorinated 1,2-dialkyl-, 1,1- and 1,2-alkylphenylbenzocyclobutenes to indan-2-one and isochromene derivatives under the action of CO/SbF5

• Carbonylation of perfluorinated 1,1- and 1,2-dialkyl- and alkylphenylbenzocyclobutenes in the system CO–SbF5.
• Formation of indan-2-one derivatives in the reaction of 1,2-disubstituted benzocyclobutenes with CO–SbF5 at 50 °C.
• Formation of isochromene derivatives at 70 °C.
• The influence of a temperature on the reaction route.

Interaction of perfluorinated 1,2-dialkylbenzocyclobutenes with CO–SbF5 at room temperature and perfluoro-1-methyl-2-phenylbenzocyclobutene at 50 °C gives fluoroindan-2-one derivatives. When reaction temperature is raised to 70 °C, polyfluorinated isochromene derivatives are formed in both cases. Interaction of perfluoro-1-ethyl-1-phenylbenzocyclobutene with CO–SbF5 at 70 °C gives, after treatment of the reaction mixture with H2O, perfluoro-3-ethyl-3-phenylindan-1,2-dione.

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