99570-28-2Relevant academic research and scientific papers
ADDITION OF CHLORINE, BROMINE AND BROMINE CHLORIDE TO SOME α,β-UNSATURATED METHYL ESTERS
Korhonen, Ilpo O. O.,Pitkaenen, Maija,Korvola, Jorma N. J.
, p. 2837 - 2841 (1982)
The additions of chlorine, bromine and bromine chloride to trans methyl 2-butenoate 1, trans methyl 2-methyl-2-butenoate 2 and methyl 3-methyl-2-butenoate 3 under ionic conditions were studied.Bromine chloride addition always gave as a major regioisomer the 2-bromo-3-chloro compound, almost quantitatively in the case of 3.The mechanism of bromonium ion ring-opening (SN1 or SN2) is discussed with respect to the double bond substitution and regioisomer proportions.The dihalo products were identified by MS, 1H and 13C NMR.
Dioxane dibromide-mediated solvent-free synthesis of vicinal dibromides
Chaudhuri, Subrata Kumar,Roy, Sanchita,Saha, Manabendra,Bhar, Sanjay
, p. 271 - 274 (2007/10/03)
Structurally varied vicinal dibromides have been synthesized in high yield and good purity through highly stereoselective anti-addition of bromine across the olefinic linkages using dioxane dibromide (DD) under solvent-free conditions. Copyright Taylor & Francis Group, LLC.
Carbon-13 NMR Spectra of Bromine-containing Esters
Velichko, F. K.,Dostovalova, V. I.,Vinogradova, L. V.,Freidlina, R Kh.
, p. 442 - 446 (2007/10/02)
13CHBrCOOR fragments of bromine-containing mono- and dicarboxylates show 13C NMR signals in the range 38-45 ppm, at 12-15 ppm to high field of their chloro analogues.The introduction of one bromine atom into the α-CH2 group causes a 6-13 ppm shift of the carbon signal, depending on the type of ester.The replacement of H with Br in 13C2H2(COOR)2 has only a negligible influence on the 13CH2 signal position.The 13CBr2COOR fragment signals appear in the range 40-54 ppm. 13C NMR data, including the chemical shift values, signal multiplicities and spin-spin couplings, make possible the identification of isomers present in isomer mixtures of bromine-containing esters.The 13COOR chemical shifts of diastereomers of α,β-dibromoesters differ noticeably from each other, and the 13C NMR spectra can thus be used to supply preliminary information about the stereochemistry of bromine addition to α,β-unsaturated acids.
