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Theoretical study on the nucleophilic fluoroalkylation of propylene oxide with fluorinated sulfones

Ling-Li Han, Tao Liu
2013 Journal of the Serbian Chemical Society  
The paths of nucleophilic fluoroalkylation reaction of propylene oxide with PhSO 2 CYF -(Y = F, H, and PhSO 2 , respectively) in the gas phase and in Et 2 O solvent were studied theoretically. The nucleophilic fluoroalkylation of propylene oxide with fluorinated carbanions was probed by comparison of the reactivities (phenylsulfonyl)monofluoromethyl anion (PhSO 2 CHF -), the (phenylsulfonyl)difluoromethyl anion (PhSO 2 CF 2 -), and the bis(phenylsulfonyl)monofluoromethyl anion ((PhSO 2 ) 2 CF
more » ... n ((PhSO 2 ) 2 CF -). The nucleophilicity reactivity order of PhSO 2 CYF -(Y = F, H, and PhSO 2 ) is (PhSO 2 ) 2 CF -> PhSO 2 CHF -> > PhSO 2 CF 2 -, which indicates that the introduction of another electron-withdrawing phenylsulfonyl group is an effective way to significantly increase the nucleophilicity of fluorinated carbanions. For comparison, the nucleophilic addition reaction of propylene oxide with the chlorine-substituted carbanion PhSO 2 CHClwas investigated. The calculated results show that the nucleophilicity of PhSO 2 CYFis better than that of PhSO 2 CHClin the ring opening reaction with propylene oxide. The calculated results are in good agreement with the available experimental ones.
doi:10.2298/jsc120831097h fatcat:yjpvxf3g3vaflpssjuqiyv6uwm