371-76-6Relevant academic research and scientific papers
Synthesis of bis(trifluoromethyl)phenylthallium and bis(trifluoromethyl)thallium acetate. Oxidative trifluoromethylation with bis(trifluoromethyl)thallium(III) compounds
Nair,Morrison
, p. 2816 - 2820 (2008/10/08)
The reaction of Cd(CF3)2·glyme with TlPhCl2 forms TlPh(CF3)2, which is isolated in 87% yield after 72 h. If TlPh(OAc)2 is the thallium source, TlPh(CF3)2 is generated in 2 h; however, the isolated yield is lower because acetate reacts with Cd(CF3)2·glyme, resulting in CH3COF. The interaction of Cd(CF3)2·glyme with Tl(OAc)3 produces Tl(CF3)2OAc, 46%, within 45 min. The possibility of utilizing (trifluoromethyl)thallium(III) species in oxidative trifluoromethylation reactions was screened by employing several classic low-valent metallic species as substrates. The reaction of elemental mercury was the most informative, yielding Hg(CF3)2 in 77% yield in glyme but generating a mixture of HgPh(CF3) and Hg(CF3)2 when CH2Cl2 was the solvent. These results are interpreted by postulating mercury insertion into the Tl-Ph bond, resulting in PhHgTl(CF3)2, which decomposes to generate HgPh(CF3). The formation of Hg(CF3)2 is attributed to the reaction of HgPh(CF3) with TlCF3.
