%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