Trifluoro-1,3,5-triazine

Trifluoro-l5355-Triazine. Cyanuric fluoride can be produced from 2,4,6-trichloro-j -l,3,5-triaziae [108-77-0] (cyanuric... 

Halogen exchange in a flow system was necessary in order to reduce decomposition and improve yields for trifluoro-l,2,4-triazines [82JCS-(Pl)1251] and -1,2,3-triazines (88T2583). 

Addition of cyclopentene to trifluoro-1,2,4-triazine gave products arising from addition of a second molecule of olefin. This was in contrast to trichloro-l,2,4-triazine where the eventual products were predominantly pyridine derivatives [82JCS(P1)1245]. 

The efficacy of RF in stabilizing small rings is well illustrated by the fact that the azete from trifluoro-l,2,3-triazine is considerably more reactive. Trapping experiments were unsuccessful and a polymer was isolated at room temperature. The dimer (41) forms an observable anion with CsF, which confirmed the endo structure [87CC1699 90JCS(P1)975, 90JCS(P1)983], In contrast, trifluoro-l,2,4,-triazine is resistant to vapor phase photoysis and flow pyrolysis [87JCS(P1) 1251]. 

Hydroxyquinolines can be converted into the fluoro derivatives by the action of 2,4,6-trifluoro-l,3,5,-triazine (60BRP845062). 

Trichloro-l,3.5-triazine (cyanuric chloride, 5) can be converted using a sixfold excess of sulfur tetrafluoride at 250 C into 2,4,6-trifluoro-l,3,5-triazine (cyanuric fluoride, 6) with lower proportions of sulfur tetrafluoride, cyanuric chlorofluorides are formed.191... 

An almost quantitative yield of (trifluoromethyl)iminosulfur diiluoride (1), a gas stable up to 600°C, can be obtained by reacting 2,4,6-trifluoro-l,3,5-triazine (cyanuric fluoride) with sulfur tetrafluoride in the presence of cesium fluoride at 1553C.203... 

Method A 4 Cl2 was passed through SbF3 (100g, 0.54mol) at 100"C until no more Cl2 was absorbed. The SbF3Cl2 which formed was allowed to cool to rt and 2,4,6-trichloro-l, 3,5-triazine (1 50 g. 0.26 mol) was added. The reaction flask was fitted with a 30-cm Vigreux column and the flask was heated until all the liquid product had distilled. Redistillation of the liquid product gave 2,4,6-trifluoro-l, 3,5-triazine (2) as a colorless liquid yield 26.1 g (71 %) bp 74 C. 

A solution of Af-Fmoc — glycine (7 0.6 g. 2 mmol) in anhyd CH2C12 (15 mL) and pyridine (162 pL, 2 mmol) was stirred under a N2 atmosphere at rt. Then, 2,4,6-trifluoro-l,3.5-triazine(2 180 pi., 2 mmol) was added and the mixture was stirred for 4 h. At that time, ice water was added to the mixture and the precipitated cyanuric acid was removed by filtration. The organic layer was separated, dried and evaporated to dryness to give crystalline A -Fmoc — Gly — F (8) yield 0.54g (91 %) mp 134-135 C. 

Trifluoro-l,3,5-triazine (13) is prepared from 2,4,6-trichloro-l,3,5-triazine (12) and sodium fluoride in refluxing tetramethylene sulfone and distilling out the product as it is formed (bp 72.5-73.5cC/760 Torr).11... 

Silver(I) fluoride is most useful for the conversion of 2-chloro-4,6-bis(pentafluoroethyl)-1,3,5-triazine, 2-chloro-4,6-bis(heptafluoropropyl)-l,3,5-triazine, and 2,4,6-trichloro-l,3,5-triazine to the corresponding fluoro-l,3,5-triazines. 2-Fluoro-4,6-bis(pentafluoroethyl)-l,3,5-triazineis obtained in 98 % yield, and 2-fluoro-4,6-bis(heptafluoropropyl)-l,3,5-triazinein 95 % yield, (both at 90 C for 30 minutes), while 2,4,6-trifluoro-l,3,5-triazine is available in 78.5% yield (at 100CC for 1 hour). Silver(II) fluoride, mercury(II) fluoride and antimony dichloride trifluoride give lower yields of these compounds.34... 

Trichloro-l,2,4-triazine (73) reacts with potassium fluoride to give the trifluoro compound (325). This reacts with hexafluoropropene to give 5-heptafluoroisopropyl-3,6-difluoro- (326), 3,5-bis(heptafluoroisopropyl)-6-fluoro- (327) and a small amount of 5,6-bis(heptafluoroisopropyl)-3-fluoro-l,2,4-triazine (328) and finally to the... 

Condensed pyridines were obtained when 1,2,4-triazines reacted with cyclic alkenes. Trichloro-l,2,4-triazine (73) afforded the condensed pyridines (370a, b) in high yield with cyclopentene and (Z)-cyclooctene, respectively. In the reaction with cyclopentene the bis adduct (371) was isolated in small amount but the bis adduct (372a) is the sole reaction product when (73) is treated with norbornene. The more reactive trifluoro-1,2,4-triazine (325) affords bis adducts (371b, c 372b) with cyclopentene and (Z)-cyclooctene as well as with norbornene (79CC658). 

Triazine furnishes the species 31 when a solution in trifluoro-acetic acid is titrated with water. The new upheld signals thus produced in PMR spectra are not seen when the hydrogen atom on C-5 is replaced by a methyl group. The hydration is reversible by basification.53 Acidification of an aqueous solution of the anhydrous sodium salt of 3-hydroxy-l,2,4-triazine precipitated a hydrate of the neutral species, and elemental analysis combined with PMR (r5 4.62) indicated structure 32. This substance was not dehydrated during sublimation or heating in distilling toluene.54... 

One of us has used molecular polarization potentials (MPP) to study the interaction of aromatic molecules, including furan, thiophene, and pyridine with a positive unitary charge, these maps being powerful tools for the study of intermolecular interactions and chemical reactivity [129,130], This kind of study leads us to examine theoretically the problem of the interaction between cations and anions with aromatic rings. We were pioneers in proposing that, in parallel with cation-7i-systems (for instance, benzene), there should exists anion-perfhiorinated-7i-systems (for instance, hexafluorobenzene) [131]. These studies include tetrafluorofuran and tetrafluorothiophene (128, 129). Simultaneously, Mascal et al. [132] described the same phenomenon but with 1,3,5-triazine (130) and 2,4,6-trifluoro-l,3,5-triazine (131) as acid 7i-systems. The group of the University of Palma de Mallorca has published a large number of papers on this topic [133] that are well summarized in a two recent reviews [134,135],... 

Thus reactions of perfluoro-2-methylpent-2-ene and perfluoro-5-azanon-4-ene with urea in the presence of triethylamine in dipolar aprotic solvents (MeCN, DMF) form 6-fluoro-4-pentafluoroethyl-5-trifluoro-methyl-l//-pyrimidin-2-one 93 and an s-triazine derivative, respectively (00JFC(103)105, 80/82JAP(K)85377). 

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