Electrophilic thallation of aniline derivatives and nitrogen heterocycles with phenylthallium(III) 18-crown-6 diperchlorate

Fumitoshi Kakiuchi, Kouichi Ohe, Naoto Chatani, Hideo Kurosawa, Shinji Murai, Yoshikane Kawasaki

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Electrophilic thallation of diphenylamine, diphenylmethylamine, triphenylamine, pyrrole, N-methylpyrrole, and pyrazole with [PhTlIII(18-crown-6)](ClO4)2 (1) gives compounds of the type [PhArTlIII(18-crown-6)](ClO4) (Ar = aryl = 4′-(phenylamino)phenyl, 4′-(methylphenylamino)phenyl, 4′-(diphenylamino)phenyl, 2′-pyrrolyl, 2′-N-methylpyrrolyl, and 4′-pyrazolyl, respectively). On the other hand, the reaction of 1 with imidazole resulted in coordination of imidazole nitrogen to the thallium ion without substitution at the ring. The character of Tl-C bonds formed by the thallation is discussed on the basis of spin-spin coupling constants between thallium nucleus and ortho protons of the phenyl group, 3JTlH2.

Original languageEnglish
Pages (from-to)752-756
Number of pages5
JournalOrganometallics
Volume11
Issue number2
Publication statusPublished - 1992
Externally publishedYes

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Thallium
thallium
aniline
imidazoles
Nitrogen
Diphenylamine
Derivatives
nitrogen
Pyrroles
spin-spin coupling
pyrroles
Protons
Substitution reactions
Ions
substitutes
nuclei
protons
rings
ions
imidazole

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Electrophilic thallation of aniline derivatives and nitrogen heterocycles with phenylthallium(III) 18-crown-6 diperchlorate. / Kakiuchi, Fumitoshi; Ohe, Kouichi; Chatani, Naoto; Kurosawa, Hideo; Murai, Shinji; Kawasaki, Yoshikane.

In: Organometallics, Vol. 11, No. 2, 1992, p. 752-756.

Research output: Contribution to journalArticle

Kakiuchi, Fumitoshi ; Ohe, Kouichi ; Chatani, Naoto ; Kurosawa, Hideo ; Murai, Shinji ; Kawasaki, Yoshikane. / Electrophilic thallation of aniline derivatives and nitrogen heterocycles with phenylthallium(III) 18-crown-6 diperchlorate. In: Organometallics. 1992 ; Vol. 11, No. 2. pp. 752-756.
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AU - Chatani, Naoto

AU - Kurosawa, Hideo

AU - Murai, Shinji

AU - Kawasaki, Yoshikane

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