Chemistry:Trifluoromethoxy group
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Short description: Functional group
The trifluoromethoxy group is the chemical group –O–CF3. It can be seen as a methoxy group –O–CH3 whose hydrogen atoms are replaced by fluorine atoms or as a trifluoromethyl group attached to the rest of the molecule by a bridging oxygen atom. Either leads to viable syntheses,[1] but in 2022 "the synthesis of CF3O- compounds suffer[ed] from restricted methods and remain[ed] difficult. In particular, the direct introduction of the CF3O motif onto organic substrates [was] still poorly described," partly because trifluoromethoxide easily decomposes to difluorophosgene.[2]
Compounds having this functional group are of some relevance as pharmaceuticals, because it is a much more hydrophobic analogue of chlorine. One example is riluzole.[3]
See also
References
- ↑ Synthetic Approaches to Trifluoromethoxy-Substituted Compounds A. Tlili, F. Toulgoat, T. Billard, Angew. Chem. Int. Ed. 2016, 55, 11726–11735; doi:10.1002/anie.201603697
- ↑ Clémence Bonnefoy, Emmanuel Chefdeville, Armen Panossian, Gilles Hanquet, Frédéric R. Leroux, et al. "Study of a stable "trifluoromethoxide anion solution" arising from 2,4-dinitro-trifluoromethoxybenzene. Chemistry - A European Journal, 2021, 27 (64), pp. 1–2. (HAL pagination). doi:10.1002/chem.202102809. ⟨hal-03582991⟩.
- ↑ Marrec, Olivier; Billard, Thierry; Vors, Jean-Pierre; Pazenok, Sergii; Langlois, Bernard R. (September 22, 2010). "A new and direct trifluoromethoxylation of aliphatic substrates with 2,4-dinitro(trifluoromethoxy)benzene". Adv. Synth. Catal. (Wiley) 352. doi:10.1002/adsc.201000488.
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