Nucleophilic reactivity towards electrophilic fluorinating agents: reaction with N-fluorobenzenesulfonimide ((PhSO 2) 2 NF)

JM Antelo, J Crugeiras, JR Leis, A Ríos

文献索引：Antelo, Juan M.; Crugeiras, Juan; Leis, J. Ramon; Rios, Ana Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 10 p. 2071 - 2076

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被引用次数: 20

摘要

Second-order rate constants for the reaction of N-fluorobenzenesulfonimide (FBS) with nucleophilic reagents, kNu (M− 1 s− 1), have been measured in aqueous solution at 25° C. Analysis of the reaction products shows that soft polarizable nucleophiles (I−, SCN−, Br−) react at fluorine, whereas hard nucleophiles (oxygen and nitrogen nucleophiles) react at sulfur. The ambident behaviour of this electrophile seems to be related to the relative ...