The Reaction of 1,3,5-Trichloro-2,4,6-trioxo-hexahydro-s-triazine with Tetrahydrofuran and Related Cyclic Ethers¹

Applications of N-Chlorosuccinimide in Organic Synthesis

“…As opposed to NCS, TCCA chlorinates esters and cyclic ethers (THF, dioxane), and aliphatic ethers are oxidized to esters, and this imposes limits on the use of several common solvents. 7 Because of the large volume of work encompassing NCS, this review focuses on the most representative and recent applications of the reagent published until the end of 2006. The chemistry and applications of N-bromosuccinimide (NBS) have been amply reviewed, 8-12 but a comparison of the reactivity of NCS with that of other Nhalosuccinimides is presented herein.…”

Trichloroisocyanuric Acid as a Cohalogenating Reagent: An Efficient Transformation of Alkenes into Chlorohydrins, β-Chloroethers and β-Chloroacetates

“…These include reactions with an oxazolinoazetidinone derivative, 13 steroids derivatives, 14 and unsaturated cyclic ethers. 15 To the best of our knowledge, there is no systematic work in the literature on the utilization of trichloroisocyanuric acid as a cohalogenat-ing reagent, and we now communicate our results in this area.…”

Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton–Todd Reaction under Base-Free Conditions

“…Trichloroisocyanuric acid (TCCA) is an inexpensive commercially available solid mainly reported to use for oxidation, chlorination, and dehydrogenation reactions. [11][12][13][14][15][16][17][18] To the best of our knowledge, there is no report on the synthesis of phosphoroamidates by the reaction of amines with dialkyl phosphates in the presence of TCCA in a one-pot manner. Therefore, we decided to study the feasibility of the TCCA as a safe reagent for the synthesis of phosphoroamidates under base-free conditions (Scheme 1).…”