Naphthalenes trifluoromethyl

The most common situation where this effect is seen is in a comparison of E- and Z- isomers of trifluoromethyl- or difluoromethyl-substituted alkenes, but as the naphthalene examples indicate, the effect is not unique to that situation. 

Finally, a few miscellaneous compounds which were identified in the Delaware River and which have not been previously reported as water contaminants will be discussed Chloro (trifluoromethyl) aniline and chloro (trifluoromethyl) nitrobenzene (no. 55 and 56) were identified in the water, they had maximum concentrations at river mile 78. Both compounds represent common sub-structures in various pesticide and dye molecules, and several of the companies located along the river have patents using these compounds (30-32j. It is possible that these compounds are actually present in the river water as such, but it is also possible that they are formed in the GC injection port by pyrolytic degradation of larger pesticide or dye molecules (see above). All three binaphthyl-sulfone isomers (no. 92) were identified in the river water near Philadelphia. Product literature for one of the companies in the area indicates production of condensed sulfonated polymers derived from naphthalene sulfonic acid and maleic anhydride. It seems likely that the binaphthylsulfones are formed as by-products during preparation of this commercial product. 

Both compounds crystallize with the cadmium diiodide structure (space group P3ml) as previously reported on polycrystalline samples.3 For platinum disulfide, ao = 3.542(1) A and c0 = 5.043(1) A, and for platinum ditelluride, a0 = 4.023(1) A and c0 = 5.220(3) A. Direct chemical analysis for the component elements was not carried out. Instead, precision density and unit-cell determinations were performed to characterize the samples. The densities of both compounds as determined by a hydrostatic technique with heptadecafluorodeca-hydro-l-(trifluoromethyl)naphthalene as the density fluid4 indicated that they are slightly deficient in platinum. For platinum disulfide, = 7.86 g/cm3 and Pmeas = 7.7(1) gm/cm3, and for platinum ditelluride, p = 10.2 gm/cm3 and Pmeas = 9.8(1) gm/cm3. In a typical experiment an emission spectrum of the platinum disulfide showed that phosphorus was present in less than 5 ppm. A mass spectroscopic examination of the platinum ditelluride revealed a small doping by sulfur (less than 0.4%) and traces of chlorine and phosphorus (less than 100 ppm). 

Reaction of naphthalene, anthracene and pyrene derivatives with trifluoromethyl hypofluorite at — 78 C results mainly in fluoro-substituted products 36 and difluoro ketones 37. The ratio between the two types of products depends on the substituents and the structure of the aromatic molecule.58-61... 

By heating with antimony(Ill) fluoride at 150°C, l,4-dichloro-2-(trichloromethyl)naphthalene is converted into l,4-dichloro-2-(trifluoromethyl)naphthalene in 75% yield.16 l-Chloro-2-(tri-fluoromethyl)naphthalene is obtained in 90% yield by refluxing the corresponding 2-trichlo-romethyl analog with antimony(III) fluoride in chlorobenzene for 9 hours.17... 

Synthesis of 1,3-disubstituted naphthalenes is a non-trivial exercise. In an interesting approach to such compounds it was found that they could be assembled by a simple two-step operation as follows. Condensation of 2-(trifluoromethyl)benzaldehyde with pentan-3-one gave the expected aldol product as the (E)-isomer, treatment of which with lithium 4-methylpiperazide in ether at -10°C led directly to l-methylpiperazino-3-propionylnaphthalene in 30% yield. 

Substituted naphthalenes have been fluorinated with trifluoromethyl hypofluorite to a mixture of two products, i.e. products 13 resulting from substitution of the hydrogen in the 1-position by fluorine and l,l-difluoronaphthalen-2(l//)-one (14). ... 

HYDROXY-3-(1,2,3,4-TETRAHYDRO-3-(4-(4-(TRIFLUOROMETHYL)PHEN-OXY) PHENYL)-1-NAPHTHALEN-YL)2H-1 -BENZOPYR AN-2-ONE mf C32H23F3O4 mw 528.55 SAFETY PROFILE A poison by ingesdon. When heated to decomposidon it emits toxic vapors of F". 

Methylisophosphinoline (3-methyl-2-phosphanaphthalene, 3-methyl-benzo[c]phosphorin) (8), m.p. 64.5-69°, is prepared by the route illustrated below (H.G. de Graaf et at.. Tetrahedron Letters, 1973, 2397). The Diels-Alder reaction between 3-methylisophosphinoline (8) and hexafluorobut-2-yne yields adduct (9), which on heating gives tarry material and 2,3-bis(trifluoromethyl)naphthalene (10) (30%) (T.C Klebach, L.A.M. Turkenburg, and F. Bickelhaupt, ibid., 1978, 1099). 

HF elimination to afford dienes [319] ortl o-Trifluoromethyl phenylacetates of Wang resin (353) can eliminate HF under basic conditions, such as LDA, to give very reactive dienes. The latter can react with the anion of benzyl cyanide or other suitable anions to give substituted l-carboxy-2-amino naphthalenes (357). In the solution phase, only self-condensation reactions can be observed. The condensation reaction is assumed to proceed in a stepwise, anion-mediated fashion (Scheme 74). 

Absorption and emission spectra of benzene, naphthalene, anthracene, and tetracene in a variety of n-perfluoroalkenes have been interpreted and the extent of solvent-solute interaction in these four systems assessed. Solvatochroraic shifts in trifluoromethyl derivatives of benzene and naphthalene show that the change in polarizability of the solute consequent upon elefctronic excitation is surprisingly small. It is found to be only 10% greater than for the ground state and the induced dipole of the excited state is close to the ground state value. 

Beilstein Handbook Reference) BRN 2030021 EINECS 206-191-9 Flutec PP9 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-Heptadecafluorodeca-hydro-6(trifluoromethyl)naphthalene Heptadecafluoro-decahydro-1-(trifluoromethyl)naphthalene Naphthalene, heptadecafluorodecahydro-l-(trifluoromethyl)- PP 9. Afluorinated hydrocarbon. 

Hydroquinone Bisphenol A, and 4 -hydroxy phenyl-4-hydroxybenzoate 4,4 -Dihydroxybenzophenone PEEK oligomer Catechol (4-(4 -Trifluoromethyl)phenoxyphen-yl)hydroquinone and hydroquinone 4,4 -Difluorodiphenyl ketone 4,4 -Difluorodiphenyl ketone 4,4 -Dichlorodiphenyl sulfone" 1,5-Bis-(4-(4 -fluorobenzoyl)-phen-oxy)-naphthalene (1,5-BFPN) 4,4 -Difluorodiphenyl ketone 4,4 -Difluorodiphenyl ketone ... 

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