Tetraethylammonium trichloride

Room-temperature ionic liquids may be used as green recyclable alternatives to chlorinated solvents for stereoselective halogenation.577 The bromination of alkenes and alkynes in [bmim][Br] is a/m -stereospecific, whereas that of 1,3-dienes gives selectively the 1,4-addition products. The reactions of arylacetylenes, however, are not selective when carried out in [bmim][PF6]. Tetraethylammonium trichloride, a stable crystalline solid may be used in the chlorination of alkenes and alkynes to afford the products with exclusive anti stereoselectivity.578 It has... 

Other reagents, providing a source of electrophilic halogen, able to selectively oxidize secondary alcohols include molecular chlorine,13 molecular bromine,13c 3-iodopyridine dichloride,13a trichloroisocyanuric acid (TCIA),14 the complex HOF MeCN15 and tetraethylammonium trichloride.16... 

There have been a number of reports of ring halogenation, the majority of which concentrate on fluorination. There was only one report of chlorination which involved the use of tetraethylammonium trichloride in an unusual mode of reaction as chlorination might be expected to occur on R rather than at the 2-position (Equation 24) <1997AGE2342>. 

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. 

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