15679-00-2

Upstream product

• 515-84-4 Ethyl trichloroacetate 
• 75-64-9 tert-butylamine 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 144396-00-9 2-t-Butyl-3-(trichloromethyl)oxaziridine 
• 116-16-5 1,1,1,3,3,3-hexachloro-propan-2-one 
• 3657-07-6 trichloroacetic acid butyl ester 
• 81171-26-8 N-(2,2,2-Trichloroethylidene)-t-butylamine 

Downstream Products

• 196861-70-8 (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester 
• 105340-30-5 2-(bromomethyl)benzoic acid t-butyl ester 
• 287178-88-5 N-Benzyloxycarbonyl-L-serine(O-tert-butyl) 2-bromoethyl ester 
• 132866-45-6 N-Benzyloxycarbonyl-L-seryl(O-tert-butyl)-glycine tert-butyl ester 
• 72289-51-1 tert-butyl (2S,3R)-2-(benzyloxycarbonyl)amino-3-hydroxybutanoate 
• 108052-76-2 4-(bromomethyl)benzoic acid 1,1-dimethylethyl ester 
• 583833-75-4 6-bromo-2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester 
• 15943-43-8 N-tert.-Butyl-dichloracetamid 

Relevant academic research and scientific papers

Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides

The rearrangement of allylic trichloroacetimidates is a well-known transformation, but the corresponding rearrangement of benzylic trichloroacetimidates has not been explored as a method for the synthesis of benzylic amines. Conditions that provide the tr

Activation energies of aminolysis of aliphatic esters in aprotic media

Activation enthalpies and entropies for the third-order aminolysis reaction of n-butyl formate, n-butyl-trichloroacetate and sec-butyl trifluoroacetate were determined in solvents of various polarity and π-basicity. The importance of the steric requirements of the reagents together with high activation entropy values support the assumption of cyclic transition states for the reaction. Electrophilicity of the ester and the solvent properties predetermine the reaction mechanism in the range between the pathway through a zwitterionic intermediate for the formate and the nearly concerted reaction for the trichloroacetate. The negative activation energy of an aminolysis reaction should not necessarily be attributed to a good leaving group, but can be determined by the electrophilicity of the ester and the solvent effects.

Synthesis, fragmentations and rearrangements of 3-(1-haloalkyl) oxaziridines

A variety of new 3-(1-haloalkyl)oxaziridines was synthesized by oxidation of α-chloro-, α-bromo-, α,α-dichloro-, α,α-dibromo- and α,α,α-trichloroaldimines with meta-chloroperbenzoic acid. Attempts to induce dehydrohalogenation into the elusive methyleneoxaziridines were unsuccessful. However, presumptive evidence is presented that 2-t-butyl-3-(trichloromethyl)oxaziridine is dehydrochlorinated into a transient methyleneoxaziridine, which underwent valence isomerization into an intermediate iminooxirane, the latter being fragmented into t-butyl isocyanide. Various types of reactions of the title compounds are reported. Among others, 2-alkyl-3-(1-chloro-1-methyl) ethyloxaziridines rearranged with methyllithium into 2-(N-alkyl)aminoisobutyraldehydes.

Formation of N-Substituted Trichloroacetamides from Amines and Hexachloroacetone

Procedures are described for converting primary amines into their well-crystalline trichloroacetyl-derivatives by treatment with hexachloroacetone under mild conditions.Although secondary aromatic N-methylamines are unaffected by hexachloroacetone, saturated heterocyclic amines react vigorously.A mechanistic study using 2-amino-4-t-butylthiazole showed that the reaction is first order in hexachloroacetone, second order in amine, and base-catalysed; there is no appreciable kinetic isotope (H/D) effect nor accumulation of intermediates during the reaction.A sequence which accommodates these results is suggested.