The preparation of aryl 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐imidazolyl sulfides and sulfones

Roger Egolf, Donna M. Bilder

Research output: Contribution to journalArticle

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Abstract

A series of aryl 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐imidazolyl sulfides was prepared by displacement of fluoride from the 5‐position of 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐fluoroimidazole by substituted thiophenols and by benzyl mercaptan. This displacement reaction occurs much more slowly than the corresponding previously described reactions of 4‐trifluoromethyl‐5‐fluorothiazoles and ‐oxazoles. Several solvent‐base pairs were examined; the reaction was found to work best when dimethyl sulfoxide was used as the solvent and diazabicycloundecene as the base. The sulfides were oxidized to sulfones by treatment with hydrogen peroxide in acetic acid.

Original languageEnglish (US)
Pages (from-to)541-543
Number of pages3
JournalJournal of Heterocyclic Chemistry
Volume31
Issue number2
DOIs
StatePublished - Jan 1 1994

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Sulfones
Sulfides
Oxazoles
Dimethyl Sulfoxide
Fluorides
Sulfhydryl Compounds
Acetic Acid
Hydrogen Peroxide
thiophenol

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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title = "The preparation of aryl 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐imidazolyl sulfides and sulfones",
abstract = "A series of aryl 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐imidazolyl sulfides was prepared by displacement of fluoride from the 5‐position of 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐fluoroimidazole by substituted thiophenols and by benzyl mercaptan. This displacement reaction occurs much more slowly than the corresponding previously described reactions of 4‐trifluoromethyl‐5‐fluorothiazoles and ‐oxazoles. Several solvent‐base pairs were examined; the reaction was found to work best when dimethyl sulfoxide was used as the solvent and diazabicycloundecene as the base. The sulfides were oxidized to sulfones by treatment with hydrogen peroxide in acetic acid.",
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The preparation of aryl 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐imidazolyl sulfides and sulfones. / Egolf, Roger; Bilder, Donna M.

In: Journal of Heterocyclic Chemistry, Vol. 31, No. 2, 01.01.1994, p. 541-543.

Research output: Contribution to journalArticle

TY - JOUR

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AB - A series of aryl 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐imidazolyl sulfides was prepared by displacement of fluoride from the 5‐position of 1‐(2,6‐dimethylphenyl)‐2‐phenyl‐4‐trifluoromethyl‐5‐fluoroimidazole by substituted thiophenols and by benzyl mercaptan. This displacement reaction occurs much more slowly than the corresponding previously described reactions of 4‐trifluoromethyl‐5‐fluorothiazoles and ‐oxazoles. Several solvent‐base pairs were examined; the reaction was found to work best when dimethyl sulfoxide was used as the solvent and diazabicycloundecene as the base. The sulfides were oxidized to sulfones by treatment with hydrogen peroxide in acetic acid.

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