Abstract
The reactions of CF 2CF 2OS O 2 and CF 3 CFCF 2OS O 2 with aromatic haloalkanes (RX, X Br) in the presence of silver fluoride were studied as a means for preparing novel aromatic polyfluoroalkoxysulfonyl fluorides. The following compounds have been prepared and characterized: ROCF 2CF 2SO 2F and ROCF 2CF(CF 3)SO 2F, where R is C 6H 5CH 2, o-(CF 3) 2C 6H 3CH 2, C 6F 5CH 2. Infrared, mass and nmr spectra are presented in order to support the assigned structure. In a comparative study, the reaction of CFHCF 2OS O 2 with benzyl bromide, in the presence of different metal fluorides such as silver fluoride, cesium fluoride and tris(dimethylamino)sulfonium difluorotrimethylsilicate were investigated. In all cases decomposition products such as SO 2F 2, SOF 2 and SO 2 were obtained; no desired alkoxy product was found. Attempts to prepare the silver alkoxide salt, AgOCF 2CFHSO 2F or the corresponding aromatic alkoxy derivatives were unsuccessful. Apparently the intermediate silver salt is unstable and cannot be recovered or used for nucleophilic displacement reactions.
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