629-32-3Relevant academic research and scientific papers
Impact of fluorine substituents on the rates of nucleophilic aliphatic substitution and β-elimination
Martinez, Henry,Rebeyrol, Adele,Nelms, Taylor B.,Dolbier Jr., William R.
experimental part, p. 167 - 175 (2012/03/27)
A measure of the quantitative effect of proximate fluorine substituents on the rates of SN2 and E2 reactions has been obtained through a study mainly of reactions of fluorinated n-alkyl bromides with weak base, strong nucleophile azide ion and strong base/nucleophile methoxide ion in the protic solvent methanol and the aprotic solvent, DMSO. The order of reactivity for SN2 reactions of azide in methanol at 50 °C was found to be: n-alkyl-Br > n-alkyl-CHFBr > n-perfluoroalkyl-CH2CH 2Br n-perfluoroalkyl-CH2Br > n-alkyl-CF2Br. Approximate relative rates of reaction were: 1, 0.20, 0.12, 1 × 10 -4, -5. The order of reactivity for E2 reactions was found to be: n-perfluoroalkyl-CH2CH2Br n-alkyl-CF2Br > n-alkyl-CHFBr > n-alkyl-Br. The approximate relative rates for reaction of methoxide in methanol at 50 °C were: 1100, 4.4, 1.9, 1.
