Abstract
In nonpolar solvents at a high temperature (70°C), oxo acids or their derivatives (AcClO4, CF3SO3H, etc.) were found to be efficient and selective catalysts for the synthesis of linear unsaturated dimers from o-, m-, and p-chlorostyrenes and p-methoxystyrene. Even p-methoxystyrene, having a strongly electron-donating methoxy group, was converted to a linear dimer in high yield (ca. 80 wt%). Selective linear dimerizations were also possible in a polar solvent in the presence of a common-ion salt, but in the absence of such a salt, the amount of higher oligomers increased in the products. Metal-halide catalysts (BF3OEt2, SnCl4, and EtAlCl2) gave cyclic dimers and higher oligomers as well as linear dimers under similar conditions. These results suggest that the non-dissociated species in which the carbocation interacts strongly with the counterion plays an important role in the formation of linear dimers.
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