Perfluoro-2,5-diazahexane-2,5-dioxyl and its use in polymer chemistry and in polymer cross-linking

Banks, R. E.; Eapen, Kalathil C.; Haszeldine, R. N.; Mitra, P.; Myerscough, T.; Smith, S.

doi:10.1039/c39720000833

Cited by 15 publications

(1 citation statement)

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“…Banks et al reported that an attack by dioxyl 80 on tetrafluoroethylene or hexafluoropropene led mainly to the formation of copolymers in, and also to a smaller number of adducts ( 81a , 81b ) [ 115 ]. It should be noted that the yield of 81b could rise to 63% if the reactants were mixed at room temperature and at ca.…”

Section: Seven- and Larger-membered Heterocyclesmentioning

confidence: 99%

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

et al. 2023

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The trifluoromethyl group is widely recognized for its significant role in the fields of medicinal chemistry and material science due to its unique electronic and steric properties that can alter various physiochemical properties of the parent molecule, such as lipophilicity, acidity, and hydrogen bonding capabilities. Compared to the well-established C-trifluoromethylation, N-trifluoromethylation has received lesser attention. Considering the extensive contribution of nitrogen to drug molecules, it is predicted that constructing N-trifluoromethyl (N-CF3) motifs will be of great significance in pharmaceutical and agrochemical industries. This review is mainly concerned with the synthesis of heterocycles containing this motif. In three-membered heterocycles containing the N-CF3 motif, the existing literature mostly demonstrated the synthetic strategy, as it does for four- and larger-membered heterocycles. Certain structures, such as oxaziridines, could serve as an oxidant or building blocks in organic synthesis. In five-membered heterocycles, it has been reported that N-CF3 azoles showed a higher lipophilicity and a latent increased metabolic stability and Caco-2-permeability compared with their N-CH3 counterparts, illustrating the potential of the N-CF3 motif. Various N-CF3 analogues of drugs or bioactive molecules, such as sildenafil analogue, have been obtained. In general, the N-CF3 motif is developing and has great potential in bioactive molecules or materials. Give the recent development in this motif, it is foreseeable that its synthesis methods and applications will become more and more extensive. In this paper, we present an overview of the synthesis of N-CF3 heterocycles, categorized on the basis of the number of rings (three-, four-, five-, six- and larger-membered heterocycles), and focus on the five-membered heterocycles containing the N-CF3 group.

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Section: Seven- and Larger-membered Heterocyclesmentioning

confidence: 99%