399-86-0Relevant academic research and scientific papers
REACTIONS OF HALOGEN FLUORIDES. XIII. NEW POSSIBILITIES FOR OXIDATIVE NUCLEOPHILIC FLUORINATION OF BROMINE-SUBSTITUTED ESTERS BY THE HEXACHLOROMELAMINE-HYDROGEN FLUORIDE SYSTEM
Chuvatkin, N. N.,Panteleeva, I. Yu.,Kurskii, Yu. A.,Boguslavskaya, L. S.
, p. 1450 - 1456 (2007/10/02)
Primary, secondary, and tertiary bromine atoms in bromine-substituted esters, including the bromine atoms of the CBr2 group at the α position to the ester group, are substituted effectively by a bromine atom in the hexachloromelamine-liquid hydrogen fluoride system under normal conditions.New methods were developed for the production of alkyl and fluoroalkyl 2,3-dihalogeno-2-fluoropropionates, which are key compounds in the synthesis of α-fluoroacrylates.
REACTIONS OF HALOGEN FLUORIDES XII. REACTION OF BROMINE TRIFLUORIDE WITH BROMINE-CONTAINING ESTERS. A NEW METHOD FOR THE SYNTHESIS OF FLUOROALKYL 2-FLUOROACRYLATES
Kartashov, A. V.,Chuvatkin, N. N.,Boguslavskaya, L. S.
, p. 2243 - 2248 (2007/10/02)
Being weak Lewis bases, esters reduce the reactivity of bromine trifluoride in the substitutive fluorination of organic bromine derivatives.For this reason the rate of the reaction of bromine trifluoride with bromine-containing esters depends not only on the electronic characteristics of the substituents at the reaction center but also on the basicity of the ester.As a rule, the selectivity of the reaction increases with increase in the basicity of the ester.The reaction of bromine trifluoride or chlorine monofluoride with fluoroalkyl 2,3-dibromopropionates can be used successfully for the synthesis of monomers (fluoroalkyl 2-fluoroacrylates).
REACTIONS OF HALOGEN FLUORIDES. VII. FLUORINATION OF UNSATURATED COMPOUNDS WITH BROMINE TRIFLUORIDE AND AN EQUIMOLAR MIXTURE OF BROMINE TRIFLUORIDE WITH MOLECULAR BROMINE
Boguslavskaya, L. S.,Chuvatkin, N. N.,Kartashov, A. V.,Ternovskoi, L. A.
, p. 230 - 236 (2007/10/02)
The reactions of bromine trifluoride and an equimolar mixture of bromine trifluoride and bromine with halogen-substituted alkenes and methyl α-substituted acrylates were investigated.With sufficient dilution of the substrate by Freon 113 (20-25:1) it is possible to obtain the bromofluoro and difluoro adducts with good yiels.The best results (overall yields of fluorination products 80-83percent) were obtained with alkenes containing a halogen at the multiple bond; in the case of more reactive substrates the reaction becomes nonpreparative.The bromofluorination of E- and Z-1,2-dichloroethylenes and E- and Z-1,3-dichloropropenes with pure bromine trifluoride is antistereospecific.The bromofluorination of E- and Z-1,2-dichloroethylenes by the BrF3-Br2 system gives a mixture of diastereomeric bromofluoro adducts as a result of isomerization of the initial olefins in the presence of the bromine.The formation of the difluorides of the halogenated olefins is nonstereospecific and is accompanied by migration of the halogens.
