TY - JOUR
T1 - Generation, characterization, and reactions of thionium ions based on the indirect cation pool method
AU - Shimizu, Akihiro
AU - Takeda, Keiji
AU - Mishima, Shota
AU - Saito, Kodai
AU - Kim, Songhee
AU - Nokami, Toshiki
AU - Yoshida, Jun Ichi
N1 - Publisher Copyright:
© 2015 The Chemical Society of Japan.
PY - 2016
Y1 - 2016
N2 - PhCH=S+Ar (Ar = p-FC6H4) was generated and accumulated for the first time in organic solvents that are commonly used for organic synthesis such as dichloromethane by the indirect cation pool method. The thionium ion is stable at temperatures lower than -20 °C, and reacts with carbon nucleophiles at the carbon adjacent to sulfur. The thionium ion was successfully characterized by UV, NMR, and IR measurements. Electronic structure of the thionium ion, in particular its bond character, is discussed based on the spectroscopic measurements and DFT calculations.
AB - PhCH=S+Ar (Ar = p-FC6H4) was generated and accumulated for the first time in organic solvents that are commonly used for organic synthesis such as dichloromethane by the indirect cation pool method. The thionium ion is stable at temperatures lower than -20 °C, and reacts with carbon nucleophiles at the carbon adjacent to sulfur. The thionium ion was successfully characterized by UV, NMR, and IR measurements. Electronic structure of the thionium ion, in particular its bond character, is discussed based on the spectroscopic measurements and DFT calculations.
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U2 - 10.1246/bcsj.20150323
DO - 10.1246/bcsj.20150323
M3 - Article
AN - SCOPUS:84955155797
SN - 0009-2673
VL - 89
SP - 61
EP - 66
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 1
ER -