Triethylamine tris

Chemical Designations - Synonyms 2,2 2"-Nitrilotriethanol Triethilolamine Trihydroxy-triethylamine Tris(hydroxyethy)amine Chemical Formula (HOCH2CH2)3N. 

Fluorine and sulfur (in the form of a methylthio group) are added to nucleophilic olefins with Markovnikov regwselectivity and anti stereoselectivity by di-methyl(niethylthio)sulfoninni fluoroborate and triethylamine tris(hydrogen fluoride) [777] (equation 21)... 

Electrochemical oxidation of 1,2-dihydronaphthalene or an indene in acetoni-tnle containing triethylamine tris(hydrogen fluoride) provides a mixture of tereoisomeric difluorides and vicinal fluoroacetamides [201] (equation 38)... 

Finally, in contrast to the reactions reported above, 49 reacts131 with dimethyl(methyl-thio)sulfonium fluoroborate (DMTSF) and triethylamine tris(hydrofluoride) in dichlorome-thane to give only 5% of the 1,2-addition product 122. The main products, present in 73 27 ratio, are the exo-exo and endo-exo adducts 123 and 124, formed by exclusive exo attack of the electrophile on the double bond, followed by transannular -participation in the intermediate bridged cation and final addition of fluoride to the nortricyclic cation from both the exo or endo side (equation 120). 

TRIETHANOLAMINE Triethylolamlne, Trihydroxy-triethylamine, Tris(hydroxy-ethyl)amine NL 2 1 1... 

The only systems which have achieved wide practical acceptance are hydrogen fluoride/ pyridine and triethylamine tris(hydrogen fluoride) combinations (Table 3). 

Triethylamine Tris(hydrogen Fluoride) (Franz s Reagent) 9... 

Formal replacement of hydrogen by fluorine takes place in the a-position of a ketone by treatment of enol acetates with triethylamine tris(hydrogen fluoride).51-55 The kinetically favored isomers are formed.51,55 Furthermore, benzylic positions bonded with an electron-withdrawing group (ketone, ester, nitrile, sulfonate) can be fluorinated electrochemically.51" 6-58 There are also various examples of the preparation of a-fluorosulfides front sulfides.51... 

Moreover, triethylamine tris(hydrogen fluoride) has been used to open epoxides in activated carbohydrate derivatives, e.g. formation of 18.08... 

Halofluorinations can also be carried out with transannular oxygen participation in the case of unsaturated bicyclic epoxides. Thus, 9-oxabicyclo[6.1,0]non-4-ene (7) is attacked stereo-specifically by A -halosuccinimide and triethylamine tris(hydrogen fluoride) (or 70% HF/py-ridine), to give endo,e fo-2-fluoro-6-halo-9-oxabicyclo[3.3.1]nonane 8 (main product) and eHr/o,eWo-2-fluoro-5-halo-9-oxabicyclo[4.2.1]nonane 9.194... 

Furthermore, electrophilic anti addition of /V-(phenylselanyl)phthalimide in the presence of triethylamine tris(hydrogen fluoride) has been investigated using alkenes (Table 14)216 and alkynes.217... 

Table 14. (Phenylselanyl)fluorination at C = C Bonds by. V-(Phenylselanyl)phthalimidc/Triethylamine Tris(hydrogen Fluoride) in Dichloromethane at 25 C216...

The electrophilic anti addition of benzeneselenenyl fluoride to C = C bonds has been performed in a one-pot reaction with, /V-(phenylselanyl)phthalimide/triethylamine tris(hydrogen fluoride) using disubstituted alkynes to give a-fluoro-/T(phenylselanyl)alkenes 4.217... 

It is noticeable that neither the most commonly used less acidic triethylamine tris(hydrogen fluoride) nor the more acidic Olah s reagent (70% HF/pyridine) lead to the generation of a cyclic fluoro alcohol from 2,6-dimethylhept-5-enal (7).395... 

Vinyloxiranes, when treated with A -bromosuccinimide-triethylamine tris(hydrogen fluoride) at — 10 C in dichloromethane, are converted into the corresponding (bromofluoro-ethyl)oxiranes.43 The regioselectivity and yield of the reaction are dependent on the degree of substitution of the vinyl group. 

Addition of a sulfenyl chloride to an alkene in the presence of silver fluoride affords (3-fluoro sulfides, as shown in equation (2).18 The same trans adducts can also be prepared from the sulfenyl chloride adducts and silver fluoride. An alternative procedure for the formal addition of methanesulfenyl fluoride to alkenes involves the use of dimethyl(methylthio)sulfonium tetrafluoroborate and triethylamine tris(hy-drofluoride) as in equation (3).19... 

Several groups have employed N-halosuccinimdes for the halofluorination of alkenes. Laurent and co-workers have found that triethylamine tris(hydrofluoride) is a suitable fluoride source for the halofluorination of a number of alkenes (Scheme 70).137 Other examples of halofluorinations include NBS and tetrabutylammonium fluoride as the halogen sources for the formal addition of BrF across funtionalized cyclohexenes138 and the halofluorination of alkenes and alkynes by all three N-halosuccinimides and polymer-supported HF.139... 

Boron trifluoride diethyl etherate Tetrabutylammonium hydroxide Triethylamine Tris(3,6-dioxahepyl)amine... 

The anti addition of the elements of benzeneselenyl fluoride to alkynes can be achieved by the reaction of disubstituted alkynes with A -(phenylselanyl)phthalimide and triethylamine tris-hydrofluoride. ... 

The Pinner salt (10), which is obtained by reaction of methanol and gaseous HCl with a-azidoacetonitrilc [51], reacts sequentially with triethylamine, tri-phenylphosphine and either acid chlorides or isothiocyanates to give imidazoles in moderate yields (Scheme 3.1.11) [52]. 

Treatment of aryl tellurium halides with base (ethanolic potassium hydroxide , aqueous sodium hydroxide, triethylamine , tris[(-propyl] phosphite , triphenylphosphane ) leads to the formation of diaryl ditellurium compounds (p. 273). In the hydrolytically induced disproportionation reactions, aryl tellurinic acids are the other tellurium-containing products ... 

Triethylamine tris(hydrofluoride) in the presence of DBU reacts quantitatively with 13. Contrary to all examples so far presented of 1,3,2-oxathiaphos-pholane ring opening condensations, an attack of fluoride ion on phosphorus is not stereospecific when performed with diastereomerically pure species, the mixture of diastereomeric compounds 68 is always produced [93, 94]. Oxathi-aphospholane derivatives of 3 -amino-3 -deoxythymidine 48 and 50 under treatment with triethylamine tris(hydrofluoride) in the presence of DBU, followed by detritylation with acidic ion-exchange resin, provided 3 -deoxythymi-dine-3 -N-phosphoramidofluoridate (69) and 3 -deoxythymidine-3 -N-phos-phoramidofluoridothioate (70) (Scheme 18), further purified by preparative TLC in ca. 80% yield [75]. 

Dehydrohalogenation Benzyltrimethylammonium mcsitoate. r-Butylamine. Calcium carbonate. j Uidine. Diazabicyclo[3.4.0]nonene-5. N.N-Dimethylaniline (see also Ethoxy-acetylene, preparation). N,N-Dimelhylformamide. Dimethyl sulfoxide-Potassium r-but-oxide. Dimethyl sulfoxide-Sodium bicarbonate. 2,4-Dinitrophenylhydrazine. Ethoxy-carbonylhydrazine. Ethyldicyclohexylamine. Ethyidiisopropylamine. Ion-exchange resins. Lithium. Lithium carbonate. Lithium carbonate-Lithium bromide. Lithium chloride. Methanolic KOH (see DimethylTormamide). N-PhenylmorphoKne. Potassium amide. Potassium r-butoxide. Pyridine. Quinoline. Rhodium-Alumina. Silver oxide. Sodium acetate-Acetonitrile (see Tetrachlorocyclopentadienone, preparation). Sodium amide. Sodium 2-butylcyclohexoxide. Sodium ethoxide (see l-Ethoxybutene-l-yne-3, preparation). Sodium hydride. Sodium iodide in 1,2-dimethoxyethane (see Tetrachlorocyclopentadienone, alternative preparation) Tetraethylammonium chloride. Tri-n-butylamine. Triethylamine. Tri-methyiamine (see Boron trichloride). Trimethyl phosphite. 

The bromofluorination of norbornadiene using A-bromosuccinimide in the presence of triethylamine-tris(hydrogen fluoride) complex (EtjN 3HF), a highly versatile and easy to handle source of fluoride ions, gave in near quantitative yield a mixture of exo-3-bromo-... 

In order to give the products of nucleophilic substitution by fluoride ion, the corresponding triflates 9 and 10 of the bromohydrins 6 and 7, triflic anhydride was used in the presence of pyridine and 4-dimethylaminopyridine in dichloromethane at — 35°C. A 3 2 ratio of stereoisomeric triflates was obtained no matter which starting bromohydrin was used. Then adding the triethylamine--tris(hydrofluoride) complex to the mixture at — 35 °C gave the corresponding bromofluoro-derivatives 3 and 4. ... 

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