2-aryl-5-trifluoromethyl-4-phenyl

Imidazole, 2-aryl-4-phenyl-5-trifluoromethyl-synthesis, 5, 483 Imidazole, azido-reactions, 5, 442 Imidazole, 2-azido-, 5, 415 cyclization, 6, 980 reactions, 5, 96 with sodium, 5, 442 tautomerism, 5, 371 Imidazole, benzoyl-IR spectra, 5, 30 Imidazole, 2-benzoyl-4-phenyl-... 

Other aryl sulfones that can accommodate the nucleophilic addition step also react in the same way. For example, excellent results have been obtained using 3,5-bis-(trifluoromethyl)phenyl sulfones.281... 

Using the same experimental approach, a family of enantiomerically pure oxonium ions, i.e., O-protonated 1-aryl-l-methoxyethanes (aryl = 4-methylphenyl ((5 )-49) 4-chlorophenyl ((5)-50) 3-(a,a,a-trifluoromethyl)phenyl ((5)-51) 4-(a,a,a-trifluoromethyl)phenyl ((S)-52) 1,2,3,4,5- pentafluorophenyl ((/f)-53)) and 1-phenyl-l-methoxy-2,2,2-trifluoroethane ((l )-54), has been generated in the gas phase by (CH3)2Cl -methylation of the corresponding l-arylethanols. ° Some information on their reaction dynamics was obtained from a detailed kinetic study of their inversion of configuration and dissociation. Figs. 23 and 24 report respectively the Arrhenius plots of and fc iss for all the selected alcohols, together with (/f)-40) of Scheme 23. The relevant linear curves obey the equations reported in Tables 23 and 24, respectively. The corresponding activation parameters were calculated from the transition-state theory. 

Fig. 24 Arrhenius plots for the dissociation of 0-protonated 1-aryl-1-methoxyethanes (aryl = 4-chlorophenyl ((5)-50) 3-(a,a,a-trifluoromethyl)phenyl ((5)-51) 4-(a,a,a-trifluor-omethyl)phenyl ((5 )-52) 1,2,3,4,5-pentafluorophenyl ((/ )-53) phenyl (i )-40)).

Iodine-catalysed hydroperoxidation of cyclic and acyclic ketones with aqueous hydrogen peroxide in acetonitrile is an efficient and eco-friendly method for the synthesis of gem -dihydroperoxides and the reaction is conducted in a neutral medium with a readily available low-cost oxidant and catalyst.218 Aryl benzyl selenoxides, particularly benzyl 3,5-bis(trifluoromethyl)phenyl selenoxide, are excellent catalysts for the epoxidation of alkenes and Baeyer-Villiger oxidation of aldehydes and ketones with hydrogen peroxide.219 Efficient, eco-friendly, and selective oxidation of secondary alcohols is achieved with hydrogen peroxide using aqueous hydrogen bromide as a catalyst. Other peroxides such as i-butyl hydroperoxide (TBHP), sodium... 

LDA in THF or in THF-HMPT, LiTMP in THF and KDA in THF have all been successfully used for the metallation of phenyl or m-(trifluoromethyl)phenyl vinyl selenide (Scheme 44). The deprotonation was shown to be reversible with LDA in THF and irreversible with LiTMP when performed in the same solvent. Extension of this reaction to homologous derivatives proved difficult since metallation at the allylic sites often competes. Allylic metallation is particularly favorable with aryl 1-propenyl selenides (Scheme 46) - and, whatever the conditions used (LiTMP or KDA ), with aryl 1-(2-methyl-1-propenyl) selenides (Scheme 47). In the latter case both the (Z)- and the ( )-methyl groups have been metidlated leading to the corresponding a-metalloallyl selenides (Scheme 47). - ... 

Aryl selenium compounds also form adducts with hydrogen peroxide, ArSe (O)OOH, that are able to carry out epoxidation [188,189], albeit at low rates [190,191]. Improvements can be made by substitution of the aromatic ring with electron-withdrawing trifluoromethyl groups [192], for example, to form the lizs-[3,5-Ws-(trifluoromethyl)phenyl]diselenide. 

Baeyer-VilUger oxidation. The BuO-Cu(III)-NO species formed on heating Cut with BU4NNO2 in o-xylene at 150° converts aryl isopropyl ketones and aryl trifluoromethyl ketones to hutyl esters. However, the scope of this reaction is limited, ethyl and methyl ketones give low yields of the corresponding esters and phenyl and r-butyl ketones are not oxidized at all under such conditions. ... 

Transesterification. Zwitterionic adduct of 4-pyrrolidinopyridine and an electron-deficient aryl isothiocyanate (e.g., p-nitrophenyl and 3,5-bis(trifluoromethyl)phenyl isothiocyanates) catalyzes transesterification of methyl esters, requiring only stoichiometric quantity of the alcohol. The reaction is best performed by azeotropic refluxing, with assistance of 5A-molecular sieves to absorb the liberated MeOH. 

Sterically crowded aryl bismuth compounds synthesis and characterization of bis 2,4,6-tris(tri luoromethyl)phenyl bismuth chloride and tris 2,4,6-tris(trifluoromethyl)phenyl bismuth. /. Organomet. Chem. 402 55-66. 

The reaction of a tin tetrahalide with a Grignard reagent or an organolithium compound has been used also for synthesis of the following compounds SnR4 R = cycloalkyl, alkenyl, or alkynyl, e.g., cyclopropyl,396 vinyl,397,398 trifluorovinyl,399 cis- and ms-propenyl,400 (cyclohexylethynyl) 281 substituted and unsubstituted (phenylethynyl) 282,401 ring-substituted aryl of very various types, e.g., w-(trifluoromethyl)phenyl, p-fluorophenyl,402 and pentafluor ophenyl.2 7 8... 

Aryl-6-phenyl-2-methylthio/secondary amino substituted-4(3//)-pyrimidinones were derived from a reaction of N-arylamino substituted 1,3-diaza-1,3-butadienes with substituted ketenes that was analyzed by computational methods <97T13829>. 1,3-Diazines related to 6-amino-4-chloro-5-cyano-2-(dimethylamino)pyrimidine were prepared in one-pot fashion from 1,1-diamino-2,2-dicyanoethylene and phosgeniminium chloride <97SC1223>. Pyrazolo[3,4- /]pyrimidines were derived from 4-substituted 5-aminopyrazole-l-carbothioamides <97JCR(S)352>. Amino-5-(trifluoromethyl)-l,2,4-triazole gave polysubstituted 2-... 

Catalytic synthesis of aryl trifluoromethyl ketone via RC(0)-0Ar bond cleavage is also known. Combination of Pd(OAc)2 with 3 equiv of P Bu3 catalyzes the formation of aryl trifluoromethyl ketone from phenyl trilluoroacetate and arylbo-rane (Eq. 3.12) [69]. This reaction is interpreted by RC(0)-0Ph bond oxidative addition to give (acyl)(phenoxo)palladium(II) complex, followed by metathesis (transmetallation) of phenoxopalladium species with arylborane and reductive elimination of acyl and aryl carbons to form the product. 

S. H. Chen and Y. Chen. Luminescent copoly(aryl ether)s with new electron transporting bis(3-(trifluoromethyl)phenyl)-l,3,4-oxadiazole or bis(3-(tri-fluoromethyl)phenyl)-4-(4-hexyloxyphenyl)4h-1,2,4-triazole segments. J. Polym. Set, Part A Polym. Chem., 42(23) 5900-5910, December 2004. 

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