Stereochemical Investigation of the Products of the Photoinduced Perfluoroalkylation–Dimerization of Anthracene
datasetposted on 18.09.2015, 00:00 by Emiko Nogami, Takashi Yamazaki, Toshio Kubota, Tomoko Yajima
Datasets usually provide raw data for analysis. This raw data often comes in spreadsheet form, but can be any collection of data, on which analysis can be performed.
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.