Trichloroacetic reagent

Trimethylsilyl trichloroacetate, K2CO3, 18-crown-6, 100-150°, 1-2 h, 80-90% yield.This reagent silylates phenols, thiols, carboxylic acids, acetylenes, urethanes, and /3-keto esters, producing CO2 and chloroform as byproducts. 

Bifunctional catalysis in nucleophilic aromatic substitution was first observed by Bitter and Zollinger34, who studied the reaction of cyanuric chloride with aniline in benzene. This reaction was not accelerated by phenols or y-pyridone but was catalyzed by triethylamine and pyridine and by bifunctional catalysts such as a-pyridone and carboxylic acids. The carboxylic acids did not function as purely electrophilic reagents, since there was no relationship between catalytic efficiency and acid strength, acetic acid being more effective than chloracetic acid, which in turn was a more efficient catalyst than trichloroacetic acid. For catalysis by the carboxylic acids Bitter and Zollinger proposed the transition state depicted by H. 

Aldehydes can be converted to acylals by treatment with an anhydride in the presence of BF3, other Lewis acids, proton acids, or PCI3. The reaction cannot normally be applied to ketones, though an exception has been reported when the reagent is trichloroacetic anhydride, which gives acylals with ketones without a catalyst. ... 

In these reagents chloramine T — a white powder containing approximately 25 % active chlorine - is used as a substitute for hypochlorite or chlorine gas. The reactions take place in either acid (hydrochloric acid, sulfuric acid, trichloroacetic acid) or alkaline medium (sodium hydroxide). 

Digitalis glycosides that react well with various chloramine T - trichloroacetic acid or mineral acid reagents are not excited to fluorescence after treatment with chloramine T — sodium hydroxide. 

The phenols pyrocatechol, resorcinol and hydroquinone can be detected with all chloramine T reagents. The detection sensitivity is about the same with chloramine T - sodium hydroxide and chloramine T - trichloroacetic acid. In all cases the detection limits are ca. 75 ng substance per chromatogram zone after the plate has been subsequently dipped in a paraffin oil solution. Somewhat less favorable detection limits of 150 to 200 ng substance per chromatogram zone are obtained after treatment with chloramine T - hydrochloric acid and chloramine T - sulfuric acid. 

Tributyltin chloride la 399,400 Tributyltin methoxide lb 319 Tributyltin oxide la 399,400 Tricarboxylic acids la 248,249 Trichloroacetic acid la 45 -, reagent la 372,420... 

Bradford reagent contains the dye Coomassie blue G-250 in an acidic solution. The dye binds to protein, yielding a blue colour that absorbs maximally at 595 nm Copper-containing reagent that, when reduced by protein, reacts with bicinchonic acid yielding a complex that displays an absorbance maximum at 562 nm Essentially involves initial precipitation of protein out of solution by addition of trichloroacetic acid. The protein precipitate is redissolved in NaOH and the Lowry method of protein determination is then performed Interaction of silver with protein - very sensitive method... 

In Goiffon s method (G3) peptides are precipitated with phospho-tungstic acid from a trichloroacetic acid filtrate. The precipitate is dissolved and color is developed by a reaction with Folins phenol reagent. This method, however, is not only specific for peptides and a separate assay of uric acid has to be made since this substance also reacts with Folin s reagent. 

The Schmidt reaction is also applied to a variety of 1-tetralones, yielding (51). The use of sodium azide in acetic acid and sulphuric acid [7, 12, 13, 30, 34, 36, 37, 72, 73, 84] is preferable to the procedure in the earlier stage, in which hydrazoic acid, sulphuric acid and chloroform are employed [115]. Other acidic reagents such as polyphosphoric acid [116, 117], sulphuric acid [116, 118], methasulphonic acid [119] and trichloroacetic acid [116] are used in some cases. Variation of substituents affects the course of the rearrangement 6-methoxytetralones are rather liable to afford the isomeric 2-benzazepine-l-ones in preference to the desired (51) [ 7, 116, 118]. The Schmidt reaction is also conveniently applied to various 1,4-naphthoquinones and yields a wide range of 2,5-dihydro-l-benzazepin-2,5-diones [85, 120-122]. 

Trimethylsilyl trichloroacetate is a useful reagent for the A-trimethylsilylation of amines284. The combined action of primary aliphatic or aromatic amines and trimethylsilyl cyanide on aliphatic or aromatic aldehydes yields a-amino nitriles (equation 93)285,286. 

Dehydrochlorination of pentachlorocyclopropane, formed from trichloroethylene and sodium trichloroacetate as a source of dichlorocarbene, yields tetrachloro-cyclopropene [150], a particularly versatile reagent for various applications. It is a reasonably reactive dienophile [151], a reagent applicable to heterocyclic synthesis [152], and an electrophile for aromatic substitutions [153] and additions to alkenes [154] in the presence of Lewis acids. 

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