Relative reactivities of halogen-substituted substrates (R-Br, R-Cl) toward the halophilic attack by a carbanion |
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Authors: | FU Weimin ZHANG Xiaojun JIANG Xikui |
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Institution: | Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, |
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Abstract: | Relative reactivities of bromine-substituted substrates (R-Br) or chlorine-substituted substrates (R-CI) toward bromophilic
or chlorophilic attack by a carbanion have been evaluated by the intermolecular competition kinetics. Relative reactivity
orders are CF3CFBr2> CF3CBr3≥CBr4 > CHBr3 > CF3CFBrCF2Br > CF2Br2 > BrCF2CF2Br > BrCH2CO2Et ≥ BrCF2CFHBr > CH2Br2 > BrCH2CH2Br, and CI3CNO2 > CI3CCN > CI3CCOPh > cyclo-C5CI6 > CI3CCOCI > CCI3CF2CI > CCI3CF3 ≥ CCI4 > CCI3CCI3 ≥ CCI3(CF2)2CI > CI3CCOCCI3 > CCI3(CF2)6CI > CI3CCO2Et > CI3CF > CI3CPh > CI3CCH2O2CCH3. |
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Keywords: | relative reactivities halogen-substituted substrates relative rates of halophilic attacks intermolecular competition kinetics |
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