Fluoromethyl-2,4,6-trinitrophenylsulfonate: A New Electrophilic Monofluoromethylating Reagent

Reichel, Marco; Sile, Sami; Kornath, Andreas und Karaghiosoff, Konstantin (2021): Fluoromethyl-2,4,6-trinitrophenylsulfonate: A New Electrophilic Monofluoromethylating Reagent. In: Journal of Organic Chemistry, Bd. 86, Nr. 6: S. 4423-4431

Abstract

Fluoromethyl-2,4,6-trinitrophenylsulfonate has been prepared for the first time and qualified as a simple to use monofluoromethylating reagent. Its molecular structure in the solid state has been determined by single-crystal X-ray diffraction studies. This reagent proves to be effective for the electrophilic introduction of a CH2F group into selected chalcogen and nitrogen nucleophiles. Monofluoromethyl derivatives of various bifunctional N,O-nucleophiles have been synthesized using fluoromethyl-2,4,6-trinitrophenylsulfonate. Due to the good crystallizing properties of the anion, the fluoromethylated products as well as side products that are difficult to identify by nuclear magnetic resonance spectroscopy can readily be characterized by X-ray crystallographic techniques.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0022-3263
• Sprache: Englisch