Stereoselective photocycloaddition reactions based on the orientation control through cation-π interactions

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Photodimerization reaction of pyridine containing alkenes were investigated both in solution and solid phases under the controlling the orientation of molecules through cation-π interactions. When irradiation of the alkene was carried out in solution, various stereoisomeric dimers were produced. On the other hand, the selectivity was significantly increased in the presence of HCl. This strongly suggests the contribution of cation-π interactions in the orientation of molecules. The solid-state reactions of the corresponding HCl salts produced HT dimers in high selectivities, also suggesting the remarkable contribution of the cation-π interactions.