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Using trichloroisocyanuric acid (TCCA) in CH2Cl2

On the basis of the above results, we have investigated the chance to perform the oxidation of unprotected a-aminoacids by trichloroisocyanuric acid (TCCA). Oxidation of a-aminoacids is an important process in the field of both synthetic organic and biological chemistry and two modes of oxidation have been developed: the oxidative transformation of an amino group into carbonyl or nitro group and oxidative decarboxylation. The first transformation can be performed as described above, using trichloroisocyanuric acid (TCCA) in CH2Cl2 on a-amino esters, followed by acidic hydrolysis. For what concerns the oxidative decarboxylation, this leads to the formation of various carbonyl compounds or nitriles of one less carbon atom depending on the reagent and reaction conditions employed: N-bromosuccinimide and alkaline bromine have been employed with only moderate yields.
In our cases, the reaction can be performed with 2/3 equivalents of trichloroisocyanuric acid (TCCA) directly on an aqueous solution of the a-aminoacid under basic conditions (Scheme 4): after 30 minutes to one hour, the nitriles can be recovered quantitatively without any trace of by-products.
Characteristics of trichloroisocyanuric acid (TCCA):
White crystalline powder or granular solid, with a strong chlorine odor stimulus, containing more than 90% available chlorine, 25 degree water solubility of 1.2 grams, the case of acid or alkali decomposition. A method for using a sterile environment, drinking water, livestock feeders and the like. Powder for the preparation of 4-6 mg / kg concentrations of disinfection of drinking water, environmental concentrations of 200-400 mg kg solution / utensils disinfection.