NMR Study of Protonated Halothiophenes. I. 1H NMR Study of Chlorothiophenium Ions

Well-resolved 1H NMR signals of the cations formed from chlorothiophenes were observed in the HSO3F or AlCl3–HCl–CH2Cl2 system. Chlorothiophenes are protonated exclusively at the position adjacent to sulfur, either with or without substituents. The protonation of 2-chloro-5-methylthiophene occurs at...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 56; no. 8; pp. 2208 - 2211
Main Authors Yokoyama, Yukihiro, Yamashita, Yukihide, Takahashi, Kensuke, Sone, Tyo
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.08.1983
Chemical Society of Japan
Subjects
Atomic and molecular physics
Exact sciences and technology
Molecular properties and interactions with photons
Nuclear resonance and relaxation
Physics
Substituent effect
Chemical solution
Five membered ring
Chemical shift
Sulfur heterocycle
Organic cation
Protonation
Experimental study
NMR spectrum
Halogen Organic compounds
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Summary:Well-resolved 1H NMR signals of the cations formed from chlorothiophenes were observed in the HSO3F or AlCl3–HCl–CH2Cl2 system. Chlorothiophenes are protonated exclusively at the position adjacent to sulfur, either with or without substituents. The protonation of 2-chloro-5-methylthiophene occurs at the 5-position, and, in the HSO3F system, the cation 5H-2-chloro-5-methylthiophenium ion thus formed undergoes an irreversible 2,5-hydrogen shift.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.56.2208