Generation, characterization, and reactions of thionium ions based on the indirect cation pool method

Akihiro Shimizu, Keiji Takeda, Shota Mishima, Kodai Saito, Songhee Kim, Toshiki Nokami, Jun Ichi Yoshida

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)61-66
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume89
Issue number1
DOIs
Publication statusPublished - 2016

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Cations
Ions
Carbon
Nucleophiles
Methylene Chloride
Sulfur
Discrete Fourier transforms
Organic solvents
Electronic structure
Nuclear magnetic resonance
thionium
Temperature

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Generation, characterization, and reactions of thionium ions based on the indirect cation pool method. / Shimizu, Akihiro; Takeda, Keiji; Mishima, Shota; Saito, Kodai; Kim, Songhee; Nokami, Toshiki; Yoshida, Jun Ichi.

In: Bulletin of the Chemical Society of Japan, Vol. 89, No. 1, 2016, p. 61-66.

Research output: Contribution to journalArticle

Shimizu, Akihiro ; Takeda, Keiji ; Mishima, Shota ; Saito, Kodai ; Kim, Songhee ; Nokami, Toshiki ; Yoshida, Jun Ichi. / Generation, characterization, and reactions of thionium ions based on the indirect cation pool method. In: Bulletin of the Chemical Society of Japan. 2016 ; Vol. 89, No. 1. pp. 61-66.
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