458. Perfluoroalkyl derivatives of nitrogen. Part XV. The reaction of trifluoronitrosomethane with trifluoroethylene, vinylidene fluoride, vinyl fluoride, and ethylene

Banks, R. E.; Haszeldine, R. N.; Sutcliffe, H.; Willis, Christopher J.

doi:10.1039/jr9650002506

Cited by 6 publications

(3 citation statements)

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“…The compounds used were prepared by members of the fluorine research group of this department. The names of the five oxazetidine and the two oxazine compounds, and references to their preparation, are as follows : perfluoro-(Zrnethyl-1,2-oxazetidine),7 4-chloro-3,3,4-trifluoromethyl-l ,Zoxazetidine,* 3,3,4-trifluoro-2-trifluoromethyl-l ,Zoxazetidine , 9 perfluor 0-(2-me t h yl-3 -me t h y lene-1 ,2-ox-azetidine),20 perfluoro-(2-methyl-3,6-dihydro-l,2-oxazine) 12 and perfluoro-(4-methyl-3-oxa-4-azabicyclo[4,2,0] oct-l(6)-ene)) .I1 All spectra were recorded on an Associated Electrical Industries Ltd. R.S.2 spectrometer, operating at 60 Mc/sec. Spectra were calibrated by the side-band modulation technique using a Muirhead D880A two-phase low frequency oscillator, incorporated in the spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Nuclear magnetic resonance studies of heterocyclic fluorine compounds. Part 1.—Oxazetidines and oxazines

Lee¹,

Orrell²

1965

Trans. Faraday Soc.

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Section: Methodsmentioning

confidence: 99%

Nuclear magnetic resonance studies of heterocyclic fluorine compounds. Part 1.—Oxazetidines and oxazines

Lee¹,

Orrell²

1965

Trans. Faraday Soc.

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“…100 °C) and the copolymer at room temperature ( Scheme 3 a). Since then, several halogenated tetrafluoroethylenes (CF 2 =CXY) have been investigated ( Scheme 3 b) [ 37 , 38 ]. It was found that the formation of an oxazetidine and the copolymer from CF 3 NO occurred most readily with the olefins CF 2 =CF 2 , CF 2 =CHF (adducts were a 99:1 mixture of 3,3,4-trifluoro-2-trifluoromethyl-1,2-oxazetidine and 3,4,4-trifluoro-2-trifluoromethyl-1,2-oxazetidine), CF 2 =CFCl, and CF 2 =CCl 2 , and less readily with perfluoro-olefins containing more than two carbon atoms, or with ethylenes containing two or more vinylic hydrogens [ 38 ].…”

Section: Four-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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“…and H (15), and C(CF3)2-O-CF2CF2 (16,17) were prepared by literature methods. AsF5 was prepared from As205 and FZ (18,19 …”

Section: Manipulation Of Volatile Materialsmentioning

confidence: 99%

Superacid-induced ring-opening reactions of fluorinated heterocycles

Kotun¹,

DesMarteau²

1989

Can. J. Chem.

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This paper is dedicated to Professor Ronald J . Gillespie on the occasion of his 65th birthday STEFAN P. KOTUN and DARRYL D. DESMARTEAU. Can. J. Chem. 67, 1724Chem. 67, (1989. HF/AsFS and HF/SbFS superacid mixtures react with fluorinated small-ring heterocycles such as 1,2-oxazetidines and oxetanes with consequent addition of HF to give alcohol and amine ring-opened products in high yield. Excess HF serves as solvent and reactant. Ring compounds containing both nitrogen and oxygen as heteroatoms protonate predominantly on nitrogen; a case with competing 0-protonation arises in the case of a chloro-substituted oxazetidine. In general, rings containing two heteroatoms retain the heteroatom-heteroatom bond and it is a carbon-heteroatom bond that opens. The resulting OH and NH functional groups are not protonated and lost in the superacid medium due to the instability of the highly fluorinated cations that would be left behind. Most of the heterocycles react at or below room temperature, although the very weakly basic 2,2-bis(trifluoromethyl)-3,3,4,4-tetrafluorooxetane requires the stronger HF/SbFS superacid system and more severe conditions. Key words: superacids, hydrogen fluoride, ring opening, fluorinated oxazetidines, fluorinated oxetanes.

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458. Perfluoroalkyl derivatives of nitrogen. Part XV. The reaction of trifluoronitrosomethane with trifluoroethylene, vinylidene fluoride, vinyl fluoride, and ethylene

Cited by 6 publications

References 0 publications

Nuclear magnetic resonance studies of heterocyclic fluorine compounds. Part 1.—Oxazetidines and oxazines

Nuclear magnetic resonance studies of heterocyclic fluorine compounds. Part 1.—Oxazetidines and oxazines

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

Superacid-induced ring-opening reactions of fluorinated heterocycles

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