The Journal of Organic Chemistry

Selective, electrophilic fluorinations using N-fluoro-o-benzenedisulfonimide

FA Davis, W Han, CK Murphy

Index: Davis, Franklin A.; Han, Wei; Murphy, Christopher K. Journal of Organic Chemistry, 1995 , vol. 60, # 15 p. 4730 - 4737

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Citation Number: 146

Abstract

The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an “electrophilic” fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3). NFOBS (2) is prepared in three steps in 81% overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10% Fflz). Reaction of 2 with ...