%0 Journal Article %A Nogami, Emiko %A Yamazaki, Takashi %A Kubota, Toshio %A Yajima, Tomoko %D 2015 %T Stereochemical Investigation of the Products of the Photoinduced Perfluoroalkylation–Dimerization of Anthracene %U https://acs.figshare.com/articles/journal_contribution/Stereochemical_Investigation_of_the_Products_of_the_Photoinduced_Perfluoroalkylation_Dimerization_of_Anthracene/2130205 %R 10.1021/acs.joc.5b01655.s004 %2 https://acs.figshare.com/ndownloader/files/3764008 %K ci %K energy barrier %K perfluoroalkyl iodide %K atropisomer %K Stereochemical Investigation %K dihydroanthracene rings %K diastereomer %K isomers %K NMR %K trifluoromethyl groups %K tran %K AnthraceneThe photoinduced perfluoroalkylation %K analysis %X The photoinduced perfluoroalkylation of anthracene has been shown to provide 9,9′,10,10′-tetrahydro-10,10′-diperfluoroalkyl-9,9′-bianthracenes in over 70% yields, each perfluoroalkyl iodide producing three diastereomers. The structures of all three diastereomers (cis,cis, cis,trans, and trans,trans isomers) have been elucidated by both NMR and X-ray crystallographic analyses. Most notably, an X-ray crystallographic analysis has revealed that the trans,trans diastereomer having the two trifluoromethyl groups in 10,10′-positions adopts a 74° twisted relationship of the two dihydroanthracene rings. Furthermore, each of the two trans,trans isomers 2a,b has been shown to exist as a mixture of new types of atropisomers and the energy barrier for the interconversion of the two atropisomers has been estimated to be 12 kcal/mol by variable-temperature NMR analysis. %I ACS Publications