TY - JOUR
T1 - Synthesis and properties of S,R-alternating octinaphthalenes
AU - Takaishi, Kazuto
AU - Sue, Daisuke
AU - Kuwahara, Shunsuke
AU - Harada, Nobuyuki
AU - Kawabata, Takeo
AU - Tsubaki, Kazunori
N1 - Funding Information:
The authors are sincerely grateful to Mr. Kazuhiro Hayashi (Kyoto University) for the dipole calculations. This study was partly supported by Grant-in-Aid for Scientific Research (KAKENHI) (17659004) and the Japan Securities Scholarship Foundation (JSSF).
PY - 2009/8/1
Y1 - 2009/8/1
N2 - (S,R,S,R,S,R,S)- and (S,R,S,S,S,R,S)-octinaphthalenes were synthesized by oxidative coupling of (S,R,S)-quaternaphthalene, and differences due to axis chirality of (S,R,S,R,S,R,S)-, (S,R,S,S,S,R,S)-, (S,S,S,R,S,S,S)-, and (S,S,S,S,S,S,S)-octinaphthalenes were compared using the Rf values on TLC, specific optical rotations, 1H NMR chemical shifts of the hydroxy groups, and CD spectra. A clear CD additivity was found in the Δε values of the 1La transition around 290 nm, which are proportional to the difference between the numbers of S and R binaphthalene units.
AB - (S,R,S,R,S,R,S)- and (S,R,S,S,S,R,S)-octinaphthalenes were synthesized by oxidative coupling of (S,R,S)-quaternaphthalene, and differences due to axis chirality of (S,R,S,R,S,R,S)-, (S,R,S,S,S,R,S)-, (S,S,S,R,S,S,S)-, and (S,S,S,S,S,S,S)-octinaphthalenes were compared using the Rf values on TLC, specific optical rotations, 1H NMR chemical shifts of the hydroxy groups, and CD spectra. A clear CD additivity was found in the Δε values of the 1La transition around 290 nm, which are proportional to the difference between the numbers of S and R binaphthalene units.
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U2 - 10.1016/j.tet.2009.05.040
DO - 10.1016/j.tet.2009.05.040
M3 - Article
AN - SCOPUS:67649547743
SN - 0040-4020
VL - 65
SP - 6135
EP - 6140
JO - Tetrahedron
JF - Tetrahedron
IS - 31
ER -