Trichloroisocyanuric acid (TCCA)

Abstract

(A) Amides, lactams and carbamates of α-amino acids can be easy transformed into the corresponding N-chlorinated compounds through reaction with TCCA, under mild reaction conditions. (B) Primary alcohols are oxidized to acids using stoichiometric TCCA and catalytic RuCl3 in the presence of n-Bu4NBr and K2CO3 in MeCN/H2O. Secondary alcohols are oxidized to ketones in the same set using MeCN/H 2O or EtOAc/H2O. Effects of pH, solvent and base were also studied. (C) Oxidation of 1,3,5-trisubstituted pyrazolines to the corresponding pyrazoles is achieved using TCCA under both heterogeneous and solvent-free conditions. (D) Combination of TCCA and catalytic TEMPO in CH2Cl 2 leads to the conversion of primary alcohols into aldehydes. In the presence of acetone, NaBr and NaHCO3, acids are obtained. Secondary alcohols are oxidized to ketones. (E) Dinitrophenols are obtained upon reaction of phenols with TCCA, NaNO2 and wet SiO2 under solid-phase reaction via in situ generation of HNO2. (F) Epoxides can be produced in mild conditions by reaction of alkenes with trichloroisocyanuric acid in aqueous acetone followed by treatment of resulting chlorohydrin with aqueous KOH in Et2O/pentane. (G) Primary amines are successfully converted into nitriles by means of TCCA and catalytic TEMPO under mild conditions. Other functional groups remain unaffected. (H) Amino acids are cleanly and efficiently converted into nitriles by means of a decarboxylation reaction carried out with TCCA in water or methanol in the presence of pyridine. Using TCCA, (S)-(+)-2-methylbutyronitrile is obtained at the highest optical purity. (I) Aldoximes derived from an o-protected vanillin, when treated with TCCA in the presence of olefins as dipolarophiles, afford nitrile oxides. Subsequent 1,3-dipolar cycloaddition generates the corresponding isoxazolines. © Georg Thieme Verlag Stuttgart.