927-84-4Relevant articles and documents
Anderson,Fox
, p. 4313 (1967)
Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide
Dix, Stefan,Golz, Paul,Schmid, Jonas R.,Riedel, Sebastian,Hopkinson, Matthew N.
supporting information, p. 11554 - 11558 (2021/07/09)
Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.
Synthesis and properties of trifluoromethoxyl fluoroformyl anhydride, CF3OC(O)OC(O)F
Manetti, Martín M.,Argüello, Gustavo A.,Paci, Maxi A. Burgos
experimental part, p. 16 - 20 (2012/10/08)
In the present work the synthesis of the trifluoromethoxyl fluoroformyl anhydride is presented for the first time. Two strategies were employed to obtain CF3OC(O)OC(O)F: the thermal decomposition of CF 3OC(O)OOOC(O)F in excess of CO, and the reaction between CF 3OC(O)OOC(O)F, FC(O)OOC(O)F and CO. A mechanism was proposed taking into account reaction rates and thermal stability of the intermediates. DFT calculations at B3LYP/6-311+G* level were used to explore the conformational space of this molecule and the relative populations of conformers at room temperature, and to simulate the experimental vibrational spectrum. This molecule completes the family of the asymmetric oxygen bonded acyl compounds CF3OC(O)OxC(O)F with x = 1-3.
The use of perfluoroalkyl hypofluorites for an efficient synthesis of perfluorinated ethers characterized by low Ostwald coefficient
Navarrini, Walter,Venturini, Francesco,Sansotera, Maurizio,Ursini, Maurizio,Metrangolo, Pierangelo,Resnati, Giuseppe,Galimberti, Marco,Barchiesi, Emma,Dardani, Patrizia
, p. 680 - 685 (2008/12/22)
In the reaction between perfluoroolefins and perfluoroalkylhypofluorites the existence of two different free radical reaction mechanisms is demonstrated by the presence of characteristic byproducts. These kinetic schemes can be experimentally controlled b