Bis(trifluoromethyl)cadmium·glyme (glyme = dimethoxyethane), a new, powerful fluoroalkylating agent and low-temperature source of difluorocarbene

Abstract

The newly isolated reagent (CF₃)₂Cd·glyme [glyme =(MeOCH₂)₂] readily exchanges ligands with, e.g., GeI₄, SnI₄, or PI₃ to form the fully substituted compounds (CF₃)₄Ge, (CF₃)₄Sn, or (CF₃)₃P, within minutes at ambient temperature; reactions with acyl halides, like MeC(O)Br, form the acyl fluorides, like MeC(O)F, in excellent yields, 95%, at –25 °C and extrusion of CF₂ at –25 °C in this reaction in indicated by the formation of the expected difluorocyclopropane from tetramethyl ethylene in 53% yield.