102276-50-6

Upstream product

• 100-46-9 benzylamine 
• 931109-52-3 O-tosyl-N-trichloroethoxycarbonylhydroxylamine 
• 108-88-3 toluene 
• 112380-59-3 Carbonic acid 2,2,2-trichloro-ethyl ester 6-trifluoromethyl-benzotriazol-1-yl ester 
• 107292-16-0 β,β,β-Trichloroethyl S-3,6-Diisopropylpyrazin-2-ylthiolcarbonate 
• 107292-13-7 3,6-Diisopropyl-2-β,β,β-trichloroethoxycarbonyloxypyrazine 
• 147357-90-2 C₁₈H₁₅Cl₃N₂O₆ 

Downstream Products

• 14117-22-7 N-benzyl-N′-butylurea 
• 69805-79-4 N-benzyl-N’,N’-morpholinylurea 
• 13143-43-6 1-(4-phenylmethyl)-3-(4-methylphenyl)urea 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups

Amino groups are selectively protected in good yields by reaction with O-Alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.

Nickel/Photoredox Dual Catalytic Cross-Coupling of Alkyl and Amidyl Radicals to Construct C(sp3)-N Bonds

The construction of C(sp3)-N bonds via direct radical-radical cross-coupling under benign conditions is a desirable but challenging approach. Herein, the cross-coupling of alkyl and amidyl radicals to build aliphatic C-N bonds in a concise, mild, and oxid

N-tosyloxycarbamates as reagents in rhodium-catalyzed C-H amination reactions

Metal nitrenes for use in C-H insertion reactions were obtained from N-tosyloxycarbamates in the presence of an inorganic base and a rhodium(II) dimer complex catalyst. The C-H amination reaction proceeds smoothly, and the potassium tosylate that forms as a byproduct is easily removed by filtration or an aqueous workup. This new methodology allows the amination of ethereal, benzylic, tertiary, secondary, and even primary C-H bonds. The intramolecular reaction provides an interesting route to various substituted oxazolidinones, whereas the intermolecular reaction gives trichloroethoxycarbonyl-protected amines that can be isolated with moderate to excellent yields and that cleave easily to produce the corresponding free amine. The development, scope, and limitations of the reactions are discussed herein. Isotopic effects and the electronic nature of the transition state are used to discuss the mechanism of the reaction.

De novo synthesis of troc-protected amines: Intermolecular rhodium-catalyzed C-H amination with N-tosyloxycarbamates

The rhodium-catalyzed intermolecular C-H insertion of the nitrene derived from 2,2,2-trichloroethyl-N-tosyloxycarbamate proceeded in good to excellent yields to produce a variety of Troc-protected amines. With cyclic aliphatic alkanes, it is possible to use only 2 equiv of substrate, whereas the reaction with aromatic alkanes is run neat. Not only does the nitrene insertion proceed in benzylic, secondary, and tertiary C-H bonds but also primary C-H insertion products were obtained in good yields. Finally, the use of chiral rhodium catalysts to provide an enantioselective version of this process is discussed.

Selective Cathodic Cleavage of Unsymmetrical Imidodicarbonates, Acylcarbamates and Diacylamides

A study of the selective cathodic cleavage of one of the alkoxycarbonyl or acyl groups from various imidodicarbonates, acylamides, and diacylamides is reported.The compounds investigated include all 15 possible combinations of the following groups in unsymmetrical N,N-diprotected derivatives of benzylamine: p-nitrobenzyloxycarbonyl, trichloroethyloxycarbonyl, toluene-p-sulfonyl, benzoyl, benzyloxycarbonyl, and tert-butyloxycarbonyl which can all be electrochemically cleavaged, except the last one.Initially the compounds were examined by cyclic voltammetry in order to measure the potentials associated with the cleavage of each group and afterwards they were electrolysed at constant potential in the presence of a proton donor.The following ranges in negative potential were recorded: 1.03-1.13 V , 1.8-2.14 V (Troc), 1.75-2.41 V (Tos), 1.88-2.52 V (Bz), and 2.83-2.9 V (Z), thus occasionally revealing a drastic effect of the auxiliary group.In the eletrolytic experiments competitive attack by base occasionally led to mixtures of monoacylamides.However, all compounds apart from some of the trichloroethyloxycarbonyl derivatives could be selectively cleaved in 89-100percent yields when an appropriate proton donor was used.Tentative explanations are given for the behaviour of the compounds studied and some conclusions are drawn.

A Synthesis of a New Type of Alkoxycarbonylating Reagents from 1,1-Bis Carbonate (BTBC) and Their Reactions

1,1'-Bis carbonate (BTBC) was prepared from 1-hydroxy-6-trifluoromethylbenzotriazole and trichloromethyl chloroformate (trichloromethyl carbonochloridate).The reaction of BTBC and alcohols afforded the corresponding acti

3,6-Diisopropyl-2-hydroxypyrazine and 3,6-Diisopropyl-2-pyrazinethiol as Carriers of Some Alkoxycarbonyl Groups

Some derivatives of benzyloxycarbonylated 3,6-diisopropyl-2-hydroxypyrazine and 3,6-diisopropyl-2-pyrazinethiol were prepared and shown to be versatile benzyloxycarbonylation reagents for amines and amino acids.It was also ascertained that 3,6-diisopropyl-2-hydroxypyrazine and 3,6-diisopropyl-2-pyrazinethiol serve effectively as carriers of the β,β,β-trichloroethoxycarbonyl group.